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3-Aryl-2-bromopropanoic acid esters reacted with o-phenylenediamine, 2-sulfanylaniline, and L-cysteine to give quinoxaline, 1,4-thiazine, and thiomorpholine derivatives, respectively, containing an aryl­methyl substituent. Analogous 1,4-benzoxazine derivatives were synthesized by reactions of 3-aryl-2-bromo­propanoyl chlorides with 2-aminophenol or 2-methoxyaniline.

We report the synthesis and morphological studies of lead sulphide nanoparticles prepared from lead(II) complexes of morpholine dithiocarbamate (PbS1), thiomorpholine dithiocarbamate (PbS2), and N-(2-hydroxyethyl)phenyl dithiocarbamate (PbS3). Powder X-ray diffraction patterns (p-XRD) of the PbS nanoparticles are indexed to face-centered cubic phase of PbS. High-resolution transmission electron microscopy (HRTEM) micrograph revealed quasi-spherical PbS nanoparticles with particle size in the range 13.86–36.06 nm while scanning electron microscopy (SEM) revealed flaky/spherical/rough surface morphology. Photocatalytic degradation of methylene blue dye by the PbS nanoparticles showed degradation efficiency of 72.6 % for PbS1, 75.9 % for PbS2, and 47.4 % for PbS3. The photodegradation efficiency shows a correlation between efficiency and morphological properties. Total organic content removal by PbS2 is 69.5 % while that of PbS1 is 64.2 % and PbS3 is 40.1 %. The as-prepared PbS nanoparticles exhibited remarkable photostability in the recyclability studies.

Two polycyclic thioalkaloides dassonmycins A (1) and B (2) were isolated from Nocardiopsis dassonvillei SCSIO 40065 associated with marine sponge Petrosia sp. Structures of 1 and 2 were elucidated by comprehensive spectroscopic analysis and confirmed by single-crystal X-ray diffraction experiments, to have a 6/6/6/6-fused tetracyclic ring featuring a naphthoquinone[2,3-e]piperazine[1,2-c]thiomorpholine scaffold. Compound 2 formed a caged core through an additional ether bridge. Both compounds exhibited moderate antibacterial and cytotoxic activities.

Polymerization-induced self-assembly (PISA) is an emerging methodology for the in situ preparation of complex polymeric nanostructures in aqueous solution. However, the scope of monomers allowing morphology transitions remains limited, which is related to the low solubility of many monomers in water. Morphology transitions have therefore been restricted to more hydrophilic monomers necessitating rather long hydrophobic blocks to induce aggregation. Even longer ones are required to induce the changes of the morphology deviating from a spherical shape – a fact that limits the accessible hydrophobic domain sizes or morphologies. Here, we demonstrate that N-acryloyl thiomorpholine (NAT) represents a unique monomer which is fully miscible with water, but results in hydrophobic polymers at degrees of polymerization (DP) below 10, while morphology transitions can occur at DPs of 25 and even less. Synthesizing over 70 block copolymers in total we identified key parameters, such as hydrophilic block length, temperature, ratio of co-solvent, and concentration, influencing the self-assembly process. While the high glass transition temperature (Tg) of PNAT may cause frozen and kinetically trapped micellar cores, suitable synthesis conditions enable access to all common morphologies including spheres, worms, and vesicles as well as intermediate phases. Applying this technique, various nanostructures are reproducibly formed in situ in aqueous dispersions rendering the presented PISA system a highly versatile, new route to functional block copolymer nanostructures for various applications.

A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs.

Pt(II) and Pd(II) complexes (1 and 2, respectively) with thiomorpholine-4-carbonitrile (TM-CN), an N-substituted thiomorpholine derivative, were synthesized from tetrachlorido precursors in water. Structural analysis has shown that 1 represents the first monomeric metal complex with this ligand type with an axial M–S bond with respect to the TM-CN ring chair conformation, while in 2 a typical equatorial M–S bond position with respect to the ring chair conformation was observed. A detailed DFT investigation revealed that axial conformers are more stable for molecular forms of both metals, while intermolecular interactions in the crystals stabilize the axial conformer for Pt(II) and the equatorial conformer for Pd(II). The magnitude of this stabilization in the case of 2 is large enough to change the most stable axial conformer in the molecular form to the equatorial conformer in the crystal. Further investigation of the strength of individual intermolecular interactions revealed significant differences of some interactions between the two structures. The likely cause of the difference in the crystal structures of experimentally obtained complexes is the fact that 1 and 2 exhibit different dominant interactions: C–H/M and C–H/S are more dominant in 1 and C–H/Cl interactions are more dominant in 2. In addition, DFT calculations have shown that while the axial position of the Pt–S bond with respect to the ring chair conformation results in a significantly shorter C–H/Pt interaction distance than that in the hypothetical equatorial conformer, there is very little difference in C–H/Pd interaction distances in conformers with axial and equatorial positions of Pd–S bond with respect to the ring chair conformation. This is the peer-reviewed version of the article: Predrag Ristić, Vladimir Blagojević, Goran Janjić, Marko Rodić, Predrag Vulić, Morgan Donnard, Mihaela Gulea, Agnieszka Chylewska, Mariusz Makowski, Tamara Todorović, Nenad Filipović, Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study, Cryst. Growth Des. 2020, 20, 5, 3018–3033, DOI: [https://doi.org/10.1021/acs.cgd.9b01661] The published version: [https://cer.ihtm.bg.ac.rs/handle/123456789/4028]

Oxidation-sensitive drug delivery systems (DDS) have attracted attention due to the potential to improve efficacy and safety of chemotherapeutics. These systems are designed to release the payload in response to oxidative stress conditions, which are associated with many types of cancer. Despite extensive research on the development of oxidation-sensitive DDS, the lack of selectivity towards cancer cells over healthy cells remains a challenge. Here, we report the design and characterization of polymeric micelles containing thioether groups with varying oxidation sensitivities within the micellar core, which become hydrophilic upon thioether oxidation leading to destabilization of the micellar structure. We first used the thioether model compounds, 3-methylthiopropylamide (TPAM), thiomorpholine amide (TMAM), and 4-(methylthio)benzylamide (TPhAM), to investigate the effect of the chemical structures of the thioethers on the oxidation by hydrogen peroxide [Formula: see text]. TPAM shows the fastest oxidation followed by TMAM and TPhAM, showing that the oxidation reaction of thioethers can be modulated by changing the substituent groups bound to the sulfur atom. We next prepared micelles containing these different thioether groups within the core (TP, TM and TPh micelles). The micelles containing the thioether groups with a higher oxidation sensitivity were destabilized by [Formula: see text] at lower concentration. Micelle destabilization was also tested in human liver cancer (HepG2) cells and human umbilical vein endothelial cells (HUVECs). The TP micelles having the highest oxidation sensitivity were destabilized in both HepG2 cells and HUVECs while the TPh micelles, which showed the lowest reactivity towards [Formula: see text] , were stable in those cell lines. The TM micelles possessing a moderate oxidation sensitivity were destabilized in HepG2 cells but were stable in HUVECs. Furthermore, the micelles were loaded with doxorubicin (Dox) to evaluate their potential in drug delivery applications. Among the micelles, the TM micelles loaded with Dox showed the enhanced relative toxicity in HepG2 cells over HUVECs. Therefore, our approach to fine-tune the oxidation sensitivity of the micelles has potential for improving therapeutic efficacy and safety of drugs in cancer treatment.

4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones reacted with morpholine and thiomorpholine in ethyl acetate to give in a few minutes 3-(morpholin-4-yl)- and 3-(thiomorpholin-4-yl)-substituted 4-halofuro­[3,4-c]pyridin-1(3H)-ones.

Fungal infection is a significant global health challenge in part due to the emergence of strains exhibiting resistance to nearly all classes of antifungals. This underscores the urgent need for the development of new antifungal agents that can circumvent this burgeoning problem. For the present research, a new selected set of pyrazolo[5,1-c][1,2,4]triazine derivatives 3a–g was prepared in high yield via the reaction of N1-(5-methylpyrazol-3-yl)hydrazonoyl chloride 1 with morpholine, thiomorpholine, 4-phenylpiperidine and N-(substituted)piperazines. The new compounds were evaluated for their in vitro antifungal and antibacterial activities. The screening revealed compounds with specific activity against pathogenic fungi, including Candida albicans, Candida auris, and Cryptococcus. Compound 3d, which incorporated N-phenylpiperazine moiety, exhibited the highest growth inhibition against C. albicans with a minimum inhibitory concentration of 16 µg/mL. The compounds were superior to fluconazole in inhibiting Candida biofilm mass at sub-inhibitory concentration. Furthermore, the MTS assay confirmed that compounds 1 and 3d exhibited an excellent toxicity profile (not toxic, up to 256 μg/mL, for mammalian cells). Collectively, the presented results demonstrate that the synthesized pyrazolo-triazines warrant further exploration for potential use as antifungal agents.

Herein, we describe the synthesis and characterizations of 2,4,6-tris(thiomorpholine)-1,3,5-triazine, 2,4,6-tris(piperazine)-1,3,5-triazine and their new Sb(III) and Bi(III) complexes. Characterizations of the ligands and complexes were carried out by elemental analysis, thermogravimetric analysis (TGA), and spectroscopic methods such as infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), and single crystal X-ray. Theoretical vibrational frequencies and 1H and13C NMR chemical shifts of free ligands as well as their Sb(III) and Bi(III) complexes have been calculated using density functional theory (DFT/B3LYP and M06-2X) methods. Our theoretical results matched the corresponding experimental data and helped with the interpretation of the IR and 1H and 13C NMR spectra. The antimicrobial in vitro studies were carried out against bacterial species Staphylococcus aureus and fungal species Candida albicans, Candida tropicalis, and Candida krusei by the microdilution method. The preliminary antimicrobial evaluations indicated that Sb(III) complexes showed moderate activities against all tested strains of bacterial and fungal with minimum inhibitory concentration (MIC) in range of 512–1024 μg mL−1.

In this study, firstly N-metacrylamido thiomorpholine containing thioether group was synthesized as monomer. Then, p(AAm-co-MTM) hydrogels were prepared from the redox polymerization of acrylamide and N-metacrylamido thiomorpholine as a selective support material. p(AAm-co-MTM) hydrogel-gold nanoparticles were obtained as a result of the reduction of the selectively absorbed gold(III) ions by the hydrogel network using NaBH4 as reducing agent. All materials were characterized using techniques such as SEM, EDX, TEM and XRD analysis. It was determined that p(AAm-co-MTM)-Au composite material has high catalytic activity for the reduction of 4-nitrophenol. The activation parameters of the reduction reaction of 4-nitrophenol using NaBH4 in the presence of p(AAm-co-MTM)-Au catalyst were calculated as Ea = 38.80 kJ/mol, ΔH# = 36.16 kJ/mol and ΔS#= −161.37 J/mol K.

The reactivity of thiomorpholinium P-(4-methoxyphenyl)-N-thiomorpholin-amidodithiophosphonate (S-MorH+2)(S-Mor-adtp−) and morpholinium P-(4-methoxyphenyl)-N-morpholin-amidodithiophosphonate (O-MorH+2)(O-Mor-adtp−) towards nickel (II) dichloride hexahydrated is presented and the hydrolysis of the relevant metal complexes investigated. The hydrolytic products (S-MorH+2)2 [Ni(dtp)2]2− and (O-MorH+2)2[Ni(dtp)2]2− were characterized by means of FT-IR, 1H, and 31P NMR and XRD and the experimented P–N cleavage investigated and elucidated by means of DFT calculations. The antimicrobial activity of the neutral nickel complex [Ni(S-Mor-adtp)2] was tested against a set of Gram-positive and Gram-negative bacteria alongside with its nanodispersion in a silica matrix. The complex [Ni(S-Mor-adtp)2] did not show antibacterial activity, whilst the nano-dispersed sample [Ni(S-Mor-adtp)2]_SiO2 demonstrated inhibition to growth of Staphylococcus aureus. The nanocomposites were fully characterized by means of XRPD, TGA, SEM and dinitrogen sorption techniques.

Two new fluorescent pteridine alkaloids, tedaniophorbasins A (1) and B (2), together with the known alkaloid N-methyltryptamine, were isolated, through application of mass directed purification, from the sponge Tedaniophorbas ceratosis collected from northern New South Wales, Australia. The structures of tedaniophorbasins A and B were deduced from the analysis of 1D/2D NMR and MS data and through application of 13C NMR DFT calculations. Tedaniophorbasin A possesses a novel 2-imino-1,3-dimethyl-2,3,7,8-tetrahydro-1H-[1,4]thiazino[3,2-g]pteridin-4(6H)-one skeleton, while tedaniophorbasin B is its 2-oxo derivative. The compounds show significant Stokes shifts (~14,000 cm−1) between excitation and emission wavelengths in their fluorescence spectra. The new compounds were tested for bioactivity against chloroquine-sensitive and chloroquine-resistant strains of the malaria parasite Plasmodium falciparum, breast and pancreatic cancer cell lines, and the protozoan parasite Trypanosoma brucei brucei but were inactive against all targets at 40 µM.

Synthetic gene delivery systems employ multiple functions to enable safe and effective transport of DNA to target cells. Here, we describe metabolite-based poly(l-lysine) (PLL) modifiers that improve transfection by imparting both pH buffering and nanoparticle stabilization functions within a single molecular unit. PLL modifiers were based on morpholine (M), morpholine and niacin (MN), or thiomorpholine (TM). PLL modification with (MN) or (TM) imparted buffering function over the pH range of 5-7 both in solution and live cells and enhanced the stability of PLL DNA nanoparticles, which exhibited higher resistance to polyanion exchange and prolonged blood circulation. These properties translated into increased transfection efficiency in vitro coupled with reduced toxicity compared to unmodified PLL and PLL(M). Furthermore, PEG-PLL(MN) DNA nanoparticles transfected muscle tissue in vivo for >45 days following intramuscular injection. These polymer modifiers demonstrate the successful design of multifunctional units that improve transfection of synthetic gene delivery systems while maintaining biocompatibility.

Four silver-based coordination polymers, {[Ag(L)2](BF4)}∞ (1), {[Ag(H2BTC)(L)]·(H3BTC)}∞ (2), {[Ag2(H2BTEC)(L)2]·3.33H2O}∞ (3), and [Ag(H25SSA)(L)]∞ (4), were synthesized using thiomorpholine-4-carbonitrile (L) as the primary ligand and three aromatic polyoxoacids as coligands: trimesic (H3BTC), pyromellitic (H4BTEC), and 5-sulfosalicylic acid (H35SSA). Compounds 1 and 3 are two-dimensional, while 2 and 4 are one-dimensional. L acts as a bis-monodentate ligand, while the Ag(I) ion is three-coordinated in 2 and four-coordinated in all of the other compounds. The tetrahedral coordination of Ag(I) in 3 leads to an almost complete absence of intermolecular interactions with the metal center. All compounds show reasonable photocatalytic activity for photocatalytic degradation of mordant blue 9 dye, with reaction rates in the 0.036–0.056 min–1 range. Changes in the reaction rates can be correlated with the type and coordination of the coligand. Complex 3 exhibits photoluminescence at 77 K, while 4 exhibits photoluminescence at both room temperature and 77 K. Luminescence lifetimes indicate electronic transitions of singlet parentage, where transitions are allowed. A TD-DFT study determined the contributions of individual singlet–singlet electronic excitations to the fluorescence, indicating that metal– intraligand transitions are responsible for luminescence in both complexes. This is the peer-reviewed version of the article: Ristić, P.; Todorović, T. R.; Blagojević, V.; Klisurić, O. R.; Marjanović, I.; Holló, B. B.; Vulić, P.; Gulea, M.; Donnard, M.; Monge, M.; Rodríguez-Castillo, M.; López-de-Luzuriaga, J. M.; Filipović, N. R. 1D and 2D Silver-Based Coordination Polymers with Thiomorpholine-4-Carbonitrile and Aromatic Polyoxoacids as Coligands: Structure, Photocatalysis, Photoluminescence, and TD-DFT Study. Crystal Growth & Design 2020, 20 (7), 4461–4478. [https://doi.org/10.1021/acs.cgd.0c00287] Supplementary material: [https://cherry.chem.bg.ac.rs/handle/123456789/4206]

In this review, we summarize synthetic approaches to preparing single or fused oxazine and thiazine derivatives using solid-phase synthesis (SPS). The literature survey revealed that diverse compounds bearing variously functionalized 1,2-oxazine, 1,3-oxazine, or 1,4-oxazine scaffolds and the corresponding thiazines are accessible by SPS. The latest contributions involving the stereoselective polymer-supported syntheses of morpholines indicate that the field is continuing to expand.

Over-alkylation side products are common in the alkylation of amines by substitution. In the synthesis of the novel HIV Maturation inhibitor BMS-955176, two over-alkylation byproducts were routinely observed at the penultimate synthetic step, in which a thiomorpholine dioxide side chain was added to the core molecule by alkylation of a primary amine. These two byproducts had drastically different HPLC relative retention times, despite both containing only one additional side chain. Adding complexity to the challenge of solving their structures was the proclivity of the two byproducts to interconvert. Positive- and negative-ion HRMS, as well as isolation and 1D and 2D NMR were utilized to determine their structures. These byproducts were additionally problematic in that they led to daughter impurities at the API step.

Continuous processing enabled the highly energetic double conjugate addition of ethanolamine to divinylsulfone to prepare 2 kg of 4-(2-hydroxyethyl)thiomorpholine 1,1-dioxide, as an intermediate in the synthesis of HIV Maturation Inhibitor BMS-955176. In situ IR was employed to monitor the steady state of the transformation for increased robustness via appearance of the thiomorpholine dioxide moiety and disappearance of the divinylsulfone. Surprisingly, a series of oligomers formed as intermediates, which converted to product with extended aging or heating, consistent with computational predictions. By running this process in flow, the highly exothermic reaction could be safely executed in an equal volume of water as the only solvent, despite an adiabatic temperature rise of 142 °C, leading to a streamlined and efficient process.

Two naphthalimide-based fluorescent probes containing a thiomorpholine (Np-NS) or a sulfoxide-morpholine (Np-NSO) component are reported. The morpholine unit of non-fluorescent Np-NS and Np-NSO can transform into sulphone-morpholine and be accompanied by blue fluorescence upon oxidative stress, ascribed to the formation of sulphone-morpholine on probes. This sensing behavior displays that they can selectively respond to glutathione to generate a green emission by a sulfonamide-based detection moiety both in vitro and in living cells. Interestingly, the different oxidation states of a sulphur atom on a thiomorpholine ring can be utilized to regulate responsiveness of these probes towards glutathione. Such an oxidation strategy would provide a possibility for enhancing the response rate.

Novel chemotherapeutic agents against multidrug resistant-tuberculosis (MDR-TB) are urgently needed at this juncture to save the life of TB-infected patients. In this work, we have synthesized and characterized novel isatin hydrazones 4(a-o) and their thiomorpholine tethered analogues 5(a-o). All the synthesized compounds were initially screened for their anti-mycobacterial activity against the H37Rv strain of Mycobacterium tuberculosis (MTB) under level-I testing. Remarkably, five compounds 4f, 4h, 4n, 5f and 5m (IC50 = 1.9 µM to 9.8 µM) were found to be most active, with 4f (IC50 = 1.9 µM) indicating highest inhibition of H37Rv. These compounds were further evaluated at level-II testing against the five drug-resistant strains such as isoniazid-resistant strains (INH-R1 and INH-R2), rifampicin-resistant strains (RIF-R1 and RIF-R2) and fluoroquinolone-resistant strain (FQ-R1) of MTB. Interestingly, 4f and 5f emerged as the most potent compounds with IC50 of 3.6 µM and 1.9 µM against RIF-R1 MTB strain, followed by INH-R1 MTB strain with IC50 of 3.5 µM and 3.4 µM, respectively. Against FQ-R1 MTB strain, the lead compounds 4f and 5f displayed excellent inhibition at IC50 5.9 µM and 4.9 µM, respectively indicating broad-spectrum of activity. Further, molecular docking, ADME pharmacokinetic and molecular dynamics simulations of the compounds were performed against the DNA gyrase B and obtained encouraging results.

At the end of 2019, the world was struck by the COVID-19 pandemic, which resulted in dire repercussions of unimaginable proportions. From the beginning, the international scientific community employed several strategies to tackle the spread of this disease. Most notably, these consisted of the development of a COVID-19 vaccine and the discovery of antiviral agents through the repositioning of already known drugs with methods such as de novo design. Previously, methylthiomorphic compounds, designed by our group as antihypertensive agents, have been shown to display an affinity with the ACE2 (angiotensin converting enzyme) receptor, a key mechanism required for SARS-CoV-2 (severe acute respiratory syndrome coronavirus 2) entry into target cells. Therefore, the objective of this work consists of evaluating, in silico, the inhibitory activity of these compounds between the ACE2 receptor and the S1 subunit of the SARS-CoV-2 spike protein. Supported by the advances of different research groups on the structure of the coronavirus spike and the interaction of the latter with its receptor, ACE2, we carried out a computational study that examined the effect of in-house designed compounds on the inhibition of said interaction. Our results indicate that the polyphenol LQM322 is one of the candidates that should be considered as a possible anti-COVID-19 agent.

Schistosomiasis is a neglected tropical disease caused by blood flukes of the genus Schistosoma and causes severe morbidity in infected patients. In 2018, 290.8 million people required treatment, and 200,000 deaths are reported per year. Treatment of this disease depends on a single drug, praziquantel (PZQ). However, in the past few years, reduced sensitivity of the parasites toward PZQ has been reported. Therefore, there is an urgent need for new drugs against this disease. In the past few years, we have focused on a new substance class called biaryl alkyl carboxylic acid derivatives, which showed promising antischistosomal activity in vitro. Structure-activity relationship (SAR) studies of the carboxylic acid moiety led to three promising carboxylic amides (morpholine, thiomorpholine, and methyl sulfonyl piperazine) with an antischistosomal activity down to 10 µM (morpholine derivative) and no cytotoxicity up to 100 µM. Here, we show our continued work on this substance class. We investigated, in extended SAR studies, whether modification of the linker and the thiophene ring could improve the antischistosomal activity. We found that the exchange of the alkyl linker by a pentadienyl or benzyl linker was tolerated and led to similar antischistosomal effects, whereas the exchange of the thiophene ring was not tolerated. Our data suggest that the thiophene ring is important for the antischistosomal activity of this compound class.

A new selective probe containing the thiomorpholine unit (TM) was synthesized and examined for the fluorescence-based detection of hypochlorous acid (HOCl). Connection of TM with the fluorophore, 7-nitrobenz-2-oxa-1,3-diazole (NBD) effectively suppresses NBD fluorescence, whereas a HOCl-induced oxidation of TM to its S-oxide turns on a green emission. HPLC analysis shows that the reaction is stoichiometric and no sulfone is formed. Moreover, neither hydrogen peroxide nor peroxynitrite are able to oxidize the probe. Experimental data indicates that NBD-TM probe can be used to detect HOCl generated by myeloperoxidase (MPO). Presented results may be helpful in developing a novel class of fluorescent and luminogenic probes for the imaging of HOCl.

Design and application of novel Rhodamine B amide derivatives achieved especially with simple secondary amines, and furthermore exhibiting fluorescence property and anticancer activity is not reported elsewhere. Further functionalization of rhodamine B at the carboxylic acid group with selected secondary amines generated amides, avoiding cyclization and simultaneously sustaining fluorescence. Currently, we have designed and developed three well defined novel rhodamine B amide derivatives by reacting rhodamine B (RHB) with thiomorpholine, bis-(2-chloroethyl) amine and morpholine (the side chains of several anticancer drugs) via rhodamine B acid chloride which resulted in fluorophores namely rhodamine B thiomorpholine amide (1), rhodamine B bis(2-chloroethyl)amine amide (2) and rhodamine B morpholine amide (3). All the three RHB amides were thoroughly characterized using analytical techniques like FT-IR, Mass, 1H NMR, 13C NMR spectroscopy and HPLC. Obtained compounds displayed molecular material attributes as well as anticancer activity. The wavelength of maximum absorption and emission of solutions occurred at ~560 nm and ~583 nm. Quantum yields (Φf = 0.40) and average fluorescence decay (~1.60 ns) of amides was comparable to RHB (1.72 ns). Optical bandgap of solids revealed semiconducting property (~ 2.9 eV). Acquired rhodamine B amides were found to be insensitive over a wide range of pH i.e. from 2 to 10 suggesting their plausible utility in biological labeling, moreover, showed potential anticancer activity against B16F10 (murine melanoma cells), MDA-MB231 (human breast cancer cells), A549 (human lung cancer cells) while they displayed less toxicity to normal HEK 293 (human embryonic kidney) cells. Interestingly, the cellular uptake study manifested that more quantity of the compound were taken up by the cancer cells compared to normal cells which indicate that these amides might become potential candidates to be developed as theranostic agents.