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PurposeThis work aims to synthesize a series of novel acyclic and/or heterocyclic systems, as precursors for dyes with potential antimicrobial activity that could be used for simultaneous dyeing and antimicrobial textile finishing. Thus, a series of novel pyridine, thiophene and pyrazolo[3,4-b]pyridine derivatives were synthesized, and their antimicrobial and textile finishing properties were studied and evaluated.Design/methodology/approachThe synthesis, structure elucidation and antimicrobial activities of the newly synthesized compounds based on 4,4-dicyano-3-phenyl-but-3-enoic acid phenylamide (1) were demonstrated. The minimal inhibitory concentration in μg/mL of the compounds showed significant antimicrobial activity against most of the tested organisms. On the other hand, their spectral characteristics and fastness properties were measured and evaluated. Antimicrobial activities of the dyed fabrics in terms of inhibition zones (mm) were measured and evaluated.FindingsA series of novel heterocyclic compounds (Schemes 1-3) were synthesized based on starting material (1). Compounds (1), 2, 4a, 8a and 9c exhibited comparable or even higher antibacterial activities than the selected standards (ampicillin), while compounds 2, 3c, 3d, 4a and 8b revealed higher antifungal activities than the selected standard (cycloheximide). On the other hand, some dyes showed high antimicrobial evaluation on the dyed fabrics (nylon 66, acetate and polyester) expressed as size (mm) of inhibition zones (Tables I-IV).Practical implicationsResults revealed that many hydrazo and azo derivatives were synthesized from some pyridines and thiophenes. The antimicrobial evaluation and textile finishing of the newly synthesized products revealed significant and potent values of antimicrobial activity.Originality/valueAll the synthesized compounds were novel and most of them exhibited higher antimicrobial activities than the selected standards antibiotics, thus are valuable for simultaneous dyeing and antimicrobial functional finishing of textile fabrics.

This study aimed to synthesize new polymeric additives including homo- and co-polymers based on 4-methyl-2-oxo-2H-chromen-7-yl methacrylate monomer and evaluating their activity as potential antimicrobials and as pour-point depressants for modification of waxy crude oil rheology. The resultant compounds were characterized by their IR, 1H NMR and 13C NMR spectral data. The formation of the new polymers, namely, poly(7-methacryloyloxy-4-methylcoumarin) [poly(MAOMC)] homo-polymer, poly(7-methacryloyloxy-4-methylcoumarin-co-vinylacetate) [poly(MAOMC)-co-(VA)] and poly(7-methacryloyloxy-4-methylcoumarin-co- octadecyl 4-(methacryloyloxy)benzoate) [poly(MAOMC)-co-(OMAOB)] co-polymers was based on free radical polymerization. The polymerization reaction was carried at 70±2°C using 2,2’-azobisisobutyronitrile (AIBN) as an initiator and dimethylformamide (DMF)/toluene as a solvent in the case of homo-polymer [poly(MAOMC)] and co-polymer [poly(MAOMC)-co-(VA)], while polymerization proceeds at the same temperature by using benzoyl peroxide as an initiator and toluene as a solvent in the case of co-polymer [poly(MAOMC)-co-(OMAOB)] The activities of the resultant compounds as potential antibacterial agents were evaluated against the two Gram-positive (Bacillus cereus and Staphylococcus aureus), the four Gram-negative (Escherichia coli, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Salmonella typhimrium) bacterial strains, and as antifungal agents against two fungal species (Aspergillus flavus and Candids albicans). The results showed that MAOMC monomer and poly(MAOMC)-co-(OMAOB) copolymer indicated moderate potent activity towards the bacterial and fungal strains used. At the other extreme, the influence of coumarin and octadecyl benzoate based compounds on the pour-point depression and on the rheological properties of crude oil with low asphaltene content was studied. The results indicated that all three polymers exhibited very good efficiency as additives to improve the flow-ability of the tested crude oil. Moreover, the poly(MAOMC)-co-(OMAOB) co-polymer was found to exhibit the highest performance to reduce and depress the pour-point of the tested crude oil and decrease the viscosity to a large extent due to the presence of two aromatic units with the long aliphatic carbon chain in its structure.

Amira EM Abdallah, Galal H Elgemeie Department of Chemistry, Faculty of Science, Helwan University, Helwan, Cairo, Egypt Background: Over the years, pyrazolopyrimidine derivatives have been recognized as having antimicrobial activities. Recently, we reported different synthetic methods to prepare pyrazolopyrimidine derivatives as anticancer and antimicrobial agents. The studies showed that our previously reported 5-aminopyrazoles 2 act as a building block for the preparation of a variety of interesting pyrazolopyrimidines as purine analogs. Purpose: The objective of this study was to describe the direct new method for preparation of novel pyrazolo[1,5-a]pyrimidine derivatives and their corresponding cycloalkane ring-fused derivatives. Also, the new compounds were tested in vitro for their antibacterial and antifungal activity properties. Methods: Pyrazolo[1,5-a]pyrimidine derivatives were prepared by the reaction of our previously reported 5-aminopyrazoles 2 with suitable sodium salts of (hydroxymethylene) cycloalkanones and sodium salts of unsaturated ketones. Results: The structures of the new compounds were characterized according to their mass spectroscopy, 1H NMR, IR and elemental analyses. Compounds 8b, 10e, 10i, and 10n were the most active compounds against Gram-positive and Gram-negative bacterial species. Compound 10i with two moieties of 4-Br-C6H4 revealed increased reactivity compared with ampicillin as standard reference. Conclusion: About twenty two novel pyrazolo[1,5-a]pyrimidine derivatives and their corresponding cycloalkane ring-fused derivatives were prepared through the reaction of 5-aminopyrazoles 2 with different sodium salts of (hydroxymethylene) cycloalkanones and sodium salts of unsaturated ketones. The antibacterial and antifungal activities of the newly synthesized compounds were evaluated and revealed that compounds 8b, 10e, 10i, and 10n were the most active compounds against Gram-positive and Gram-negative bacterial strains. Keywords: pyrazolo[1,5-a]pyrimidines, 5-aminopyrazoles, 2-(hydroxymethylene)-1-cycloalkanones, 2-formylcycloalkanones, antibacterial, antifungal, docking studies

Reactivity of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3- carbonitrile towards thioglycolic acid resulted in thiazole derivative 1. The latter reacted with different chemical reagents to give thiazole, pyrano[2,3-d]thiazole and thiazolo[ 4,5-d]thiazole derivatives. Cytotoxicity effects of the newly synthesized products against six cancer cell lines, namely, human gastric cancer (NUGC), human colon cancer (DLD- 1), human liver cancer (HA22T and HEPG-2), human breast cancer (MCF) and nasopharyngeal carcinoma (HONE-1) as well as against a normal fibroblast cell (WI-38) were evaluated. The study showed that the 4,5,6,7 tetrahydrobenzo[ b] thiophene derivatives 6a, 7, 8a,b, 9b and 10b,c w ere t he most active compounds. Their potencies were attributed to the presence of the electron withdrawing groups.

The 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene was the key starting compound used to synthesize new thiazole, pyrimidine, pyran, pyridine and thiazine derivatives. The cytotoxicity of the synthesized compounds was studied towards the three cancer cell lines namely MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (central nervous system (CNS) cancer) in addition to the normal cell line (WI-38) using doxorubicin as the reference drug. The study showed that compounds 5, 9a, 15b, 17c, 18 and 21b were the most potent compounds.

Hetero-steroids, hybrid anticancer agents, have received much interest in view of their numerous and promising biological activities. In this study, a novel class of hetero-steroids were synthesized, analytical and spectral data proved the validity of the novel synthesized steroid derivatives. The cytotoxicity of the synthesized compounds 2, 5, 6, 7, 10, 11, 12, 14, 15, 17 were evaluated using human hepatocellular carcinoma cell lines (HepG2 and Huh-7) and non-small cell lung cancer (A549) cell lines. The synthesized compounds reported a remarkable gradual decrease in the cell viability of the three tested cancer cell lines. It was observed that compounds 2 and 12 had the lowest IC50s and the highest cytotoxic effects against all tested cell lines. As attempt to explain the cytotoxic activity achieved by the tested compounds in the in vitro study, molecular simulation was done to reveal the activity of the tested compounds against four different proteins (CDK2, CYP19, JAK2, and BCL2) which are highly implicated in cancer regulation and progression. We found that compound 2, and 12 were the best docked compounds against all tested receptors, which was indicated by lowest binding energy compared to reference ligand. Interestingly enough, our molecular study was in agreement with the cytotoxic activity. As future prospective, we are recommending further study on compounds 2, and 12 against the four different proteins to prove their mode of action.

This work was focused on an investigating of flow ability of waxy crude oil by nontraditional polymer compound. For this propose, a spirocompound consisted of benzaldehyede and triethanolamine 6,6'-(((phenylmethylene) bis (oxy)) bis (ethane-2,1-diyl)) bis (2-phenyl-1,3,6-dioxazocane) [SB] was synthesized using zeolite as a catalyst. The chemical structure of the [SB] was investigated by FT-IR, TGA,GPC, H1NMR and Mass spectroscopy. The rheological behavior and pour point depression of waxy crude oil were also studied different dosages and temperatures. The results showed a significant reduction in the viscosity at different temperatures and dosages. Moreover, it was noticed a decrease in the apparent viscosity and the Bingham yield value for [SB] 437.7, 367.1, and 307.1 cp and 0.48, 0.39 and 0.31 Pa at 15 oC, 20 oC and 30 oC and concentration 1000 ppm respectively. While the blank experiment displayed 743.1, 694.2 and 607.2 cp and 0.74, 0.69 and 0.60 Pa at the same temperatures. This study included blends between [SB] and the acrylate based polymers abbreviated as (B1, B2, B3 and B4). Furthermore, the rheological behavior and the pour point for these blends exhibited that the blend [B4] shew more reduction in the apparent viscosity than [SB] being alone. The apparent viscosity and yield value for [B4] were; 267.8, 249.2 and 212.7 cp and 0.22, 0.11 and 0.09 Pa at 15oC, 20oC and 30oC and concentration 1000 ppm respectively. The pour point depression (Δpp) of [SB] was 9oC while the blank pour point was 27 o C and the B4 was achieved the maximum depression in the pour point (Δpp= 18 o C) at a concentration of 1000 ppm. This result means that the addition of [SB] to [B4] showed the most positive synergistic effect.

Attempting to produce cyclized systems with potential anti-proliferative activity, a series of novel thiophene and benzothiophene derivatives were designed and synthesized. The reactivity of the latter derivatives towards different chemical reagents was studied. Twenty-one compounds were synthesized and evaluated as anti-cancer agents. The results showed that ethyl 5-amino-3-(4-chlorostyryl)-4-cyanothiophene-2-carboxylate (5b), ethyl 5-amino-4-((4-methoxyphenyl)carbonyl)-3-methylhiophene-2-carboxylate (8c) and 5-3-(ethoxy-3-oxopropanamido)-3-methyl-4-(phenylcarbamoyl)thiophene-2-carboxylate (9) were the most active compounds towards three tumor cell lines – MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer) and a normal fibro-blast human cell line (WI-38) compared to the anti-proliferative effects of the reference control doxorubicin.