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In this study, we conducted the synthesis and diagnosis of compound denoted as 1A3, specifically, (2E,4E,9E,11E)-7-chloro-2,12-diphenyltrideca-2,4,9,11-tetraene-6,8-dione. The photoluminescent and UV-vis spectral properties of this compound are investigated. The compound is dissolved in both chloroform and DMF for analysis purposes. Compound 1A3's nonlinear optical (NLO) characteristics when dissolved in DMF, are extensively studied through a series of experiments including diffraction patterns (DPs) and Z-scan. The optical limiting (OL) property of the 1A3 compound is tested and a threshold value of 12.4 mW at the wavelength 473 nm is obtained. Additionally, we explored its potential for all-optical switching utilizing two low-power visible laser beams. Notably, we achieved a significant nonlinear refractive index (NLRI) reaching up to 5.921 x 10-11 m2/W. To analyze the obtained diffraction patterns, we employed the Fresnel-Kirchhoff integral equation and conducted meticulous simulations. The numerical outcomes showed satisfactory agreement with the experimental observations. [ABSTRACT FROM AUTHOR]

Herein, a novel series of 1,5‐disubstituted‐1,2,3‐triazolines containing 1‐(4‐chlorobenzhydryl) piperazine moiety (8–18) were synthesised and evaluated for their anticancer activity across eight human tumor cell lines. Remarkably, compound 11 substituted with 3‐acetylphenyl group was the most potent anticancer agent against three selected human cancer cell lines (HL‐60, Z138, and DND‐41) with IC50 values of 16.80, 18.50, and 19.20 μM, respectively. In contrast, analogue 10 demonstrated activity against HL‐60, Z138, and DND‐41 cell lines, with IC50 values of 19.90, 18.00, and 18.50 μM, respectively. Moreover, derivative 13 substituted with 4‐bromophenyl moiety displayed activity with IC50=19.90 μM against the DND‐41 cell line. However, all analogues showed IC50 values ranging from 22.95 to 58.45 μM when tested against other investigated cancer cell lines. These findings suggest that derivative 11 holds promise as a potential candidate for synthesizing novel anticancer agents. Furthermore, compounds 8–18 were screened for their antioxidant activity. Molecular docking studies of compound 11 on crystal structures of two proteins, CDK2/cyclin A2 (PDB: 7B7S) and kinase Akt1 PKB alpha (PDB: 4GV1) have been studied. [ABSTRACT FROM AUTHOR]

In this work OR1(E1,6E) -1,7-bis (4-propyloxy phenyl) hepta-1,6-diene-3,5 dione compound is synthesized. The compound has been characterized via computational technique by studying the molecule's electronic structures through calculating its HOMO and LUMO energies, and its band gap energy (EHOMO-ELUMO). The nonlinear refractive index (NLRI) of the solution of OR1 compound in DMF solvent is determined using diffraction patterns (DPs) which resulted when a continuous wave laser beam of wavelength 473 nm traversed the compound solution in a glass cell of 1 mm thickness. By counting the number of rings under maximum beam input power, the NLRI of value 10− 6cm2/W resulted. The NLRI is calculated once more via the Z-scan technique and a value of 0.25 × 10− 7cm2/W is obtained. The vertical convection current in the OR1 compound solution appears to be responsible for the asymmetries noticed in the DPs. The temporal variation of each DP is noticed together with the evolution of DPs against beam input power. DPs are numerically simulated based on the Fresnel-Kirchhoff integral with good accord compared to the experimental findings. Dynamic and static all-optical switching in the OR1 compound using two laser beams (473 and 532 nm) is tested successfully. [ABSTRACT FROM AUTHOR]

A new series of derivatives (compounds 8–20) of the breast antihormonal drug letrozole tagged with additional aryl groups were synthesized starting from the letrozole analog 7 via Suzuki cross-coupling reaction. Treatment of the ketone 9 with various aldehydes in base afforded the chalcone analogs 21–27. The structural assignments were done by IR, 1H, 13C and 2D NMR spectra. Compounds 13, 21–23, 25 and 26 have been selected for their anticancer activity against MCF-7 and WRL-68 cell lines. Compounds 13 and 22 were found to be the most potent anticancer agents with IC50 values of 34.75 and 58.79 (μg mL−1) (SI = 3.3 and 2.6, respectively). Molecular docking study of compounds 13 and 22 revealed hydrogen bond with the amino acids Arg115, Met374 and Met364 residues of the receptor 3EQM, respectively. Therefore, compounds 13 and 22 can be considered as promising anticancer agents due to their potent cytotoxic activity. [ABSTRACT FROM AUTHOR]

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New pregnene analogs of N-hydroxamic acid 6, imino-propane hydrazides 7 and 8 as well as the aryl amides 9–11, oxadiazole, pyrazole and sulfinyl analogs 13–15, via the hydrazide analog 5 of methyl ((5-pregnen-3β,17β-diol-15α-yl)thio)propanoate (4) were synthesized. The in vitro cytotoxic activities of selected synthesized steroids against two human prostate cancer cell lines (PC-3, and LNCaP-AI) were evaluated by MTT assay. Compound 10 was the most active cytotoxic agent among these steroids against PC-3 and LNCaP-AI cell lines with inhibition of 96.2%, and 93.6% at concentration levels of 10.0 μM and 91.8%, and of 79.8% at concentration of 1.0 μM, respectively. Molecular docking study of 10 showed a hydrogen bonding with the amino acid Asn705 residue of the receptor 1E3G, together with hydrophobic interactions. Therefore, compound 10 can be considered as a promising anticancer agent due to its potent cytotoxic activity. [ABSTRACT FROM AUTHOR]

The development of new prostate cancer protein receptor cytochrome P450 17A1 inhibitors offers the possibility of generating structures of increased potency. To this end, the chalcone analogs 7 and 8 were prepared from treatment of methyl 3-oxo-3H-benzocoumarin-2-carboxylate (4) with aryl aldehydes. Treatment of 7 and 8 with three anti-inflammatory drugs, flurbiprofen, ketoprofen and ibuprofen, in the presence of POCl3/DMAP gave the ester analogs 9–12. Analogously, treatment of ethyl 3-oxo-3H-benzocoumarin-2-carboxylate (15), prepared previously from 2-hydroxy-1-naphthaldehyde (13) and dimethylmalonate (14), with various arylamines: 4-bromoaniline, 2-amino-6-methylpyridine, amino-antipyrine and 2-amino-5-nitrothiazole, in the presence of potassium tert-butoxide gave the benzocoumarine-3-arylamide analogs. The in vitro cytotoxic activities of 9–12 and 16–19 were evaluated against human prostate cancer cell lines (PC-3) and normal human liver epithelia (WRL-68) by MTT assay. Compounds 10 and 17 were the most active cytotoxic agents among the series against PC-3 cells with IC50 values of 71.35 and 78.25 μg mL–1 with SI values of 3.0 and 4.2, respectively (calculated from the cytotoxicity effects of 10 and 17 on the normal human liver epithelia [WRL-68]). Furthermore, compounds 11 and 12 were tested against breast cancer (HER2 cell lines), prostate cancer (DU-135 cell lines) and MCF-7 but were inactive. Molecular docking studies between the protein receptor CYPP450 17A1 and compounds 10 and 17 revealed that these compounds primarily form hydrophobic interactions with the receptor. [ABSTRACT FROM AUTHOR]

There is an urgent need for the design and development of new and safer drugs for the treatment of HIV infection, active against the currently resistant viral strains by development of new non-nucleoside reverse transcriptase inhibitors (NNRTIs). A series of pregnenolone analogues, 3-((aryl)-1-(5-pregnen-3β-ol-17-yl)prop-2-en-1-ones, were synthesized. Further, treatment of 3-((4-bromo-, 4-trifluoromethyl, or 4-methylphenyl)-1-(preg-5-en-3β-ol-17-yl)prop-2-en-1-ones with thiosemicarbazide in ethanolic KOH or hydrazine hydrate in HOAc gave 5-(4-bromo-, 4-trifluoromethyl, or 4-methylphenyl)-3-(preg-5-en-3β-ol-17-yl)-4,5-dihydro-1H-pyrazoline-1-carbothioamides and 1-O-acetyl-(5-(4-bromophenyl)-3-(preg-5-en-3β-ol-17-yl)-4,5-dihydro-1H-pyrazoline, respectively. Analogously, treatment of 3-((4-bromophenyl)-1-(preg-5-en-3β-ol-17-yl)prop-2-en-1-one with hydroxylamine afforded the Z/E isomers of 3-(4-bromophenyl)-1-(preg-5-en-3β-ol-17-yl)prop-2-en-1-one oxime. The new compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compounds 3-(thiophene-2-yl)-1-(preg-5-en-3β-ol-17-yl)prop-2-en-1-one and 1-O-acetyl-(5-(4-bromophenyl)-3-(preg-5-en-3β-ol-17-yl)-4,5-dihydro-1H-pyrazoline were the most active in inhibiting HIV-1 and HIV-2 with IC50 = 60.5 μM (SI > 2, against HIV-2 and SI < I against HIV-1), and > 0.29 μM (SI < I), respectively, suggesting to be new leads in the development of antiviral agents. QSAR of 3-((aryl)-1-(5-pregnen-3β-ol-17-yl)prop-2-en-1-ones and 5-(substituted phenyl)-3-(5-preg-5-3β-ol-17-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamides has been studied. The conformational analysis of 5-(4-trifluoromethylphenyl)-3-(preg-5-en-3β-ol-17-yl)-4,5-dihydro-1H-pyrazoline-1-carbothioamide and 1-O-acetyl-(5-(4-bromophenyl)-3-(preg-5-en-3β-ol-17-yl)-4,5-dihydro-1H-pyrazoline as well as the molecular docking study of the latter compound have been investigated. [ABSTRACT FROM AUTHOR]

1J(15N,H) coupling constants for enaminones and NH‐forms of intramolecularly hydrogen‐bonded Schiff bases as model compounds for sp2‐hybridized nitrogen atoms are evaluated using density functional theory (DFT) to find the optimal functionals and basis sets. Ammonia is used as a test molecule and its one‐bond coupling constant is compared with experiment. A methylamine Schiff base of a truncated molecule of gossypol is used for checking the performance of selected B3LYP, O3LYP, PBE, BHandH, and APFD density functionals and standard, modified, and dedicated basis sets for coupling constants. Both in vacuum and in chloroform, modeled by the simple continuum model of solvent, the modified basis sets predict significantly better the 1J(15N,H) value in ammonia and in the methylamine Schiff base of a truncated molecule of gossypol than the standard basis sets. This procure is then used on a broad set of intramolecularly hydrogen‐bonded molecules, and a good correlation between calculated and experimental one‐bond NH coupling constants is obtained. The 1J(15N,H) couplings are slightly overestimated. The calculated data show for hydrogen‐bonded NH interatomic distances that the calculated values depend on the NH bond lengths. The shorter the bond lengths, the larger the 1J(15N,H). A useful correlation between 1J(15N,H) and NH bond length is derived that enables realistic predictions of one‐bond NH coupling constants. The calculations reproduce experimentally observed trends for the studied molecules. [ABSTRACT FROM AUTHOR]

A number of 5‐acyl rhodanines and thiorhodanines with bulky acyl groups (pivaloyl and adamantoyl), not previously available, have been synthesized. The compounds are shown to exist in the enol form. Structures have been calculated using both the MP2 approach and the B3LYP‐GD3BJ functional and the 6‐311++G(d,p) basis set. Hydrogen bond energies are estimated by subtracting energies of a structure with the OH group turned 180° from those of the intramolecularly hydrogen‐bonded one. Properties such as OH chemical shifts, two‐bond isotope effects on 13C chemical shifts, electron densities at the bond critical point from atoms in molecules analysis, and the hydrogen bond energies show that the sterically hindered compounds have stronger hydrogen bonds than methyl or isopropyl derivatives. The combination of oxygen and sulfur derivatives enables a detailed analysis of hydrogen bond energies. [ABSTRACT FROM AUTHOR]

Curcumin and other three curcuminoids (bisdemethoxycurcumin, α-chlorocurcumin and α-methylcurcumin) were synthesized. Fourier transform infrared spectroscopy, Fluorescence quantum yields, AFM analysis and image surface profiles were characterized. All compounds possessed electron donor moieties at both ends of the conjugated π-system and an electron acceptor moiety in the middle of the molecules (D-A-D system) and should exhibit different optical properties depending on substituents on the benzene rings. The third order nonlinear optical properties of the curcuminoids have been investigated by z-scan technique. The optical response was characterized by measuring the refractive index (n2) of the derivatives of curcumin using the Z-scan technique. The compounds showed negative and large nonlinear refractive index values of the order of 10−7 cm2/W and reverse saturable absorption with high values of the nonlinear absorption coefficient of the order of 10−4 cm/W. The nonlinear refractive index was found to vary with the different compound. The optical constants of the different compound films were studied and the dispersion of the refractive index was discussed in terms of the Wemple-DiDomenico single oscillator model. The photo-physical properties of these compounds are compared to those of native curcumin, in order to provide a rationale to the design of samples with molecular structures optimized for a photosensitizer. These types of materials may be considering new photonic applications. [ABSTRACT FROM AUTHOR]

Five new thiophenoxyketinimines have been synthesized. 1H and 13C NMR spectra as well as deuterium isotope effects on 13C chemical shifts are determined, and spectra are assigned. DFT and MP2 calculations of both structures, chemical shifts, and isotope effects on chemical shifts are done. The combined analysis reveals that the compounds are primarily on a zwitterionic form with an NH+ and a S− group and with a little of the neutral form mixed in. Very strong intramolecular hydrogen bonding is found and very high NH chemical shifts are observed. The theoretical calculations show that calculations at the MP2 level are best to obtain correct “C═S” chemical shifts. [ABSTRACT FROM AUTHOR]

The development of new HIV non-nucleoside reverse transcriptase inhibitors offers the possibility of generating structures of increased potency. To this end, coupling of mefenamic acid (4) with 4-amino-acetophenone (6) in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine (DMAP) reagents afforded 4-(acetyphenyl)-2-((2,3-dimethylphenyl)amino)benzamide (7). Analogously, treatment of mefenamyl chloride (5) prepared from 4 with 6 under microwave irradiation (MWI) afforded 7. A new series of substituted chalconylincorporated amide derivatives of mefenamic acid 8-13 were synthesized from condensation of 7 with various substituted benzaldehydes via the Claisen-Schmidt reaction. Treatment of 8 and 11 with thiourea in a basic medium afforded the thiopyrimidine analogues 14 and 15, respectively. The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compounds 9 and 11 showed cytotoxicity values of 2.17 and 2.06 μm, respectively, against mock-infected MT-4 cells (C type adult T leukemia cells), which considered to be promising antileukemic agents. [ABSTRACT FROM AUTHOR]

A new class of 3α-ester derivatives of pregnenolone, using Mitsunobu reaction conditions, is described. The scheme involved the conversion of pregnenolone ( 4) into 20-(2-hydroxyethyl)imino-pregn-5-en-3β-ol ( 8), followed by tritylation to give the analogue 9. Treatment of 9 with various aryl carboxylic acids afforded the tritylated 3α-ester pregnenolone analogues 18-23. Detritylation with AcOH furnished the 3α-substituted aryl ester derivatives 24-29. Analogously, the 3β-ester analogues 31 and 32 were synthesized from pregnenolone ( 4) and its analogue 30, using Steglich coupling method, by treatment with rhodamine B in the presence of DCC/DMAP. These derivatives were screened for their CYP17α hydroxylase inhibition activity expressed in Escherichia coli. Compound 27 was the most active inhibitor among both series, with IC value of 1.12 μM and selectivity profile of 88.56 % inhibition of CYP17α hydroxylase enzyme. [ABSTRACT FROM AUTHOR]

A new series of 2-amino-4-benzyloxy-6-(2-fluorophenyl)pyrimidine derivatives (14-22) were synthesized via Suzuki-Miyaura cross-coupling reaction, with the aim of developing novel HIV non-nucleoside reverse transcriptase inhibitors. All the synthesized compounds were structurally confirmed by spectral analyses. The compounds were evaluated for their antiviral activity against the replication of HIV-1 and HIV-2 in MT-4 cells using an MTT assay. Compound 20 exhibited IC50 value of 1.83 µ? with SI = 10.3 against HIV-1. In a docking study, 20 interacted with several amino acids in the reverse transcriptase (RT) binding site of HIV-1, and the results suggest that 20 can be considered as a new lead in the development of antiviral agents. The structure activity relationship (SAR) of these new analogues was studied as well. In addition, the CDK2 inhibitory activity of the 5-nitrosopyrimidine analogues 23-27 and 35-38 was evaluated. [ABSTRACT FROM AUTHOR]

The reaction of potassium tellurocyanate (prepared in situ) withN-(1-chloroethylidene)arylamines (i.e., 4-RC6H4N = C(CH3)Cl, where R = H, Cl, CH3and NO2) in DMSO solution gave unexpectedly, after hydrolysis, the correspondingN-(3-(arylamino)butan-2-ylidene)arylamines in 63–78%. Reaction ofN-(3-(arylamino)butan-2-ylidene)arylamines with SOCl2or with Br2resulted in the substitution of a halogen on the aromatic rings. The presence of a water molecule within the structure of the synthesized diimines was rationalized theoretically by Density Functional Theory (DFT). All compounds were characterized by elemental analysis, IR, NMR and mass spectroscopic data. [ABSTRACT FROM AUTHOR]

Novel 2,3-dihydro-4-pyridinones were synthesized via the reaction of curcumin and primary amines or amine acetates under microwave irradiation. Montmorillonite K-10 was used as a catalyst. Reaction times did not exceed 120 s. The structures of the compounds were established by elemental analysis and from their mass, ¹H- and 13C-NMR spectra. [ABSTRACT FROM AUTHOR]

Symmetrical and non-symmetrical diimines derived from dimedone were synthesized by the reaction of their corresponding enaminothiones with primary amines. The synthesized compounds were characterized using micro analytical data and NMR spectroscopy. Theoretical calculations by B3LYP/6-31G(d,p) level of theory show that the enolic form is the most stable within the possible tautomeric forms of the compounds. [ABSTRACT FROM AUTHOR]

A number of o-hydroxy aromatic aldehydes have been synthesized to illustrate the effect of steric compression and O···O distances on the intramolecular hydrogen bond and the hydrogen bond energies. Hydrogen bond energies have been calculated using the 'hb and out' method using either the MP2 method or the B3LYP functional with the basis set 6-311++G(d,p). However, several compounds cannot be treated this way. Hydrogen bond energies are also determined using electron densities at bond critical points and these results are in good agreement with the results of the 'hb and out' model. Two-bond deuterium isotope effects on 13C chemical shifts are suggested as an experimental way to obtain information on hydrogen bond energies as they easily can be measured. Isotope effects on aldehyde proton chemical shifts have also been measured. The former show very good correlation with the hydrogen bond energies and the latter are related to short O···O distances. Short O···O distances can be obtained as the result of short C=C bond lengths, conjugative effects, and steric compression of the aldehyde group. Short O···O distances are in general related to high hydrogen bond energies in these intramolecularly hydrogen-bonded systems of resonance assisted hydrogen bond (RAHB) type. [ABSTRACT FROM AUTHOR]