Organic Communications

Year: 2020 Volume: 13 Issue:4 October-December

Review Article

1) Cycloaddition reactions of 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione (PTAD) and 4-methyl-3H-1,2,4-triazole-3,5(4H)-dione (MTAD): A short review

Org. Commun. (2020) 13:4 ; 146 - 154
by Nataliya Korol , Mikhailo Slivka and Oksana Holovko-Kamoshenkova

The sources, describing cycloaddition reactions with the participation of 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione (PTAD) and 4-methyl-3H-1,2,4-triazole-3,5(4H)-dione (MTAD) were reviewed from the middle 1970s and they are mentioned in chronological order. It was noted that the most investigated are Diels-Alder reactions and cycloaddition to a few cyclic mono- and dienes. Stereochemistry of obtained products are also described.

DOI
http://doi.org/10.25135/acg.oc.88.20.11.1870
Keywords
cycloaddition PTAD MTAD Diels-Alder reaction
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Original Article

2) Synthesis, spectral characterization, antimicrobial activity and docking studies against DNA Gyrase-A of new 4-chloro-3-nitrobenzene sulfonamide derivatives

Org. Commun. (2020) 13:4 ; 155 - 164
by K. Pushpa Kumar , Reddi Mohan Naidu Kalla , Mavallur Varalakshmi , Chintha Venkataramaiah , K.Swetha Kumari , Jayakumar Kannali , D. Venkatramana Reddy and Chamarthi Nagaraju

A series of new 4-chloro-3-nitrobenzene sulfonamide derivatives 3(a-j) were synthesized from 4-chloro-3-nitrobenzene sulfonyl chloride by reacting various amino acid esters and amines 2(a-j) in high yields. The structures of all the synthesized compounds were characterized by the IR, NMR (1H & 13C), mass and elemental analyses. Further, all the synthesized compounds were tested for the antimicrobial activity and docking studies were carried out with DNA Gyrase-A. Most of the compounds showed good to moderate antimicrobial activities and binding affinity towards DNA Gyrase-A structure.

DOI
http://doi.org/10.25135/acg.oc.90.20.11.1858
Keywords
4-Chloro-3-nitrobenzene amino acid esters antimicrobial activity docking studies DNA Gyrase A sulfonamides
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Original Article

3) Synthesis of novel potential ROCK inhibitors and their antimigratory effects

Org. Commun. (2020) 13:4 ; 165 - 174
by Sümeyye Turanlı , Azize Gizem Uslu and Aysun Özdemir

Rho kinase (ROCK), an enzyme belonging to the serine-threonine kinase family, is involved in the regulation of basic cellular processes such as morphology, movement, division, differentiation and apoptosis. On the other hand, excessively activated ROCK can cause to cardiovascular and neurological disorders or cancer. In recent years, overactivation of Rho kinases has been associated with increased metastasis in various tumor types and has been explored as target for the development of new anticancer drugs. We report here the design and synthesis of five urea derivatives in search of novel inhibitors of cancer cell migration. Compounds evaluated for their cytotoxic activities against breast (MCF-7) cancer cell line. After determination of the ineffective concentrations of compounds on the proliferation of MCF-7 cells, wound healing experiments were conducted to investigate the antimigratory effects of compounds. While compounds 4 and 10 had no effect on cell migration, treatment of MCF-7 cells with compounds 5, 8 and 9 resulted in significant reduction in cell motility. Taken together our results suggest that the newly synthesized compounds 5, 8 and 9 had the potential antimigratory activity through possible ROCK inhibition in cancer cells.

DOI
http://doi.org/10.25135/acg.oc.87.20.10.1846
Keywords
ROCK migration MCF-7 benzoxazolone benzimidazole urea
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Original Article

4) Facile microwave synthesis of a novel phenothiazine derivative and its cytotoxic activity

Org. Commun. (2020) 13:4 ; 175 - 183
by Cenk A. Andac

Herein, a facile procedure for microwave synthesis and NMR characterization of phenothiazine derivatives 10-(3-hydroxypropyl)-2-(methylsulphanyl)-10H-phenothiazine (3) (25% yield) and 1-[3-(2-methylsulfanyl-10H-phenothiazine-10-yl)-propyl]pyrimidine-2,4-(1H,3H)-dione (6) (67% yield) is described. After successful microwave synthesis steps, MTT cytotoxicity experiments gave rise to greater anticancer effect of compound 6 in MCF-7 human breast adenocarcinoma cell line (IC50= 1.35 µM) as compared to literature values for tamoxifen (IC50= 8.3 µM) and doxorubicin (IC50= 27 µM).

DOI
http://doi.org/10.25135/acg.oc.86.20.10.1853
Keywords
Microwave synthesis phenothiazine derivatives 1-(3-(2-methylsulfanyl-10H-phenothiazine-10-yl)-prop-1-yl)pyrimidine-2,4(1H,3H)-dione NMR IC50 MCF-7
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Original Article

5) Synthesis, anticancer activities and molecular modeling studies of some 2-aminonaphtho[2,3-d][1,3]thiazole-4,9-dione derivatives

Org. Commun. (2020) 13:4 ; 184 - 193
by Hülya Yanık , Sümeyra Ayan , Atİlla Akdemİr , Ömer Erdoğan , Cem Bülent Üstündağ , Özge Çevİk and Özgür Yılmaz

Quinones, especially 1,4-naphthoquinones, are one of the most significant and widely distributed phytochemical groups in nature. 1,4-Naphthoquinones and their synthetic derivatives are found to possess remarkable cytotoxic activities. In this study, a series of 2-aminonaphtho[2,3-d][1,3]thiazole-4,9-dione derivatives were synthesized and their structures were verified with spectral analysis. In vitro cytotoxic activities of the synthesized compounds were evaluated by using MTT assay against MKN-45 (Human Gastric cancer), MDA-MB-231 (Human Breast cancer) and HeLa (Human Cervical cancer) cell lines. Among the synthesized compounds, 3d inhibited MDA-MB-cell proliferation with an IC50 value of 0.276 µM. Compound 3a inhibited HeLa and MKN-45 cell proliferation with IC50 values of 0.336 µM and 8.769 µM, respectively. Compound 3b inhibited HELA cell proliferation with an IC50 value of 0.269 µM. Molecular docking results suggest that the ligands may bind to the hDNA TopoIIβ binding pocket and partially exert their effects. These results propose that 2-aminonaphtho[2,3-d]thiazole-4,9-dion core has important biological effects and further explorations are worthwhile.

DOI
http://doi.org/10.25135/acg.oc.91.20.11.1913
Keywords
2-aminonaphtho[2,3-d][1,3]thiazole-4,9-dione naphthoquinones DNA topoisomerases anticancer activity
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Communication

6) Efficient one-pot three-component synthesis of 2H-indazole [2,1-b]phthalazine-1,6,11(13H)-triones at room temperature

Org. Commun. (2020) 13:4 ; 194 - 201
by Parshuram M. Pisal , Vinod T. Kamble , Ravi Varala and Pradip B. Gujarathi

Tetrabutylammonium bromide (TBAB) and cesium carbonate (Cs2O3) catalyzed, one-pot three-component synthesis of 2H-indazole[2,1b]phthalazine-1,6,11(13H)-triones was developed at room temperature in ethanol. Both electron donating and withdrawing groups are compatible under the optimized reaction parameters.

DOI
http://doi.org/10.25135/acg.oc.85.20.08.1768
Keywords
TBAB; Cs2CO3 indazole[2,1-b]phthalazine-1,6,11(13H)-triones catalysis
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Short Communication

7) Synthesis of ɣ-glutamyl β-cyanoalanine precursor

Org. Commun. (2020) 13:4 ; 202 - 206
by Şule Şahin Ün , Ramazan Altundaş and Ahmet C. Gören

The synthesis of precursors of neurotoxic ɣ-glutamyl β-cyanoalanine was developed starting from L-Serine via through the preparation of b-cyanoalanine and glutamyl units. Coupling of these two intermediates gave methyl ester of ɣ-glutamyl β-cyanoalanine precursor.

DOI
http://doi.org/10.25135/acg.oc.89.20.05.1660
Keywords
Amino acid β-cyanoalanin (BCA) precursors of gGBCA ɣ-glutamyl β-cyanoalanine (ɡGBCA)
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