Microwave Assisted Synthesis of Novel N-(Benzo[d]Thiazol-2-yl)-2-((2,4'-Dioxospiro[Indoline-3,2'-Thiazolidin]-3'-yl)Amino)Acetamide Derivatives as Potent Antibacterial Agents

Borad, Mayuri A.; Bhoi, Manoj N.; Parmar, Jagruti A.; Patel, Hitesh D.

doi:10.18052/www.scipress.com/ILCPA.53.122

ILCPA > ILCPA Volume 53 > Microwave Assisted Synthesis of Novel...

< Back to Volume

Microwave Assisted Synthesis of Novel N-(Benzo[d]Thiazol-2-yl)-2-((2,4'-Dioxospiro[Indoline-3,2'-Thiazolidin]-3'-yl)Amino)Acetamide Derivatives as Potent Antibacterial Agents

Full Text PDF

Abstract:

As part of continuing studies in emerging new antibacterial agent, a novel series of N-(benzo[d] thiazol-2-yl)-2-((2,4’-dioxospiro[indoline-3, 2’-thiazolidin]-3'-yl)amino)acetamide derivatives were synthesized by sequencing reaction of 2-aminobenzothiazole with chloroacetyl chloride, hydrazine hydrate, isatin and Thioglycolic acid. The novel heterocycles were characterized by elemental analyses and various spectroscopic techniques. The synthesized compounds were tested in-vitro antibacterial activity against two Gram-positive and two Gram-negative bacteria. Bacteriological results showed that compound 5c possessed a broad spectrum of antibacterial activity against the tested microorganisms.

Info:

Periodical:

International Letters of Chemistry, Physics and Astronomy (Volume 53)

Pages:

122-129

DOI:

https://doi.org/10.18052/www.scipress.com/ILCPA.53.122

Citation:

M. A. Borad et al., "Microwave Assisted Synthesis of Novel N-(Benzo[d]Thiazol-2-yl)-2-((2,4'-Dioxospiro[Indoline-3,2'-Thiazolidin]-3'-yl)Amino)Acetamide Derivatives as Potent Antibacterial Agents", International Letters of Chemistry, Physics and Astronomy, Vol. 53, pp. 122-129, 2015

Online since:

July 2015

Authors:

Mayuri A. Borad, Manoj N. Bhoi, Jagruti A. Parmar, Hitesh D. Patel

Keywords:

Antibacterial Activity, Benzothiazoles, Heterocyclic Compound, Isatin, Spiro Compound

Export:

RIS, BibTeX, Text

Distribution:

Open Access

This work is licensed under a
Creative Commons Attribution 4.0 International License

References:

(a) T. Torroba, Poly-sulfur-nitrogen heterocycles via sulfur chlorides and nitrogen reagents, J. prakt. Chem., 341 (1999).

MN. Bhoi, MA. Borad, HD. Patel, Synthetic strategies for fused benzothiazoles: past, present and future, Synth. Commun., 44 (2014) 2427-2457.

T. Jiang, KL. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T. Tuntland, K. Zhang, D. Karanewsky, Y. H, Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part 2, Bioorg. Med. Chem. Lett., 16 (2006).

M. Verma, S. Nath Pandeya, K. Nand Singh, JP. Stables, Anticonvulsant activity of Schiff bases of isatin derivatives, Acta Pharm., 54 (2004) 49-54.

A. Amal Raj, R. Raghunathan, MR. Sridevikumaria, N. Raman, Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines, Bioorg. Med. Chem., 11 (2003) 407- 419.

R. Tripathy, A. Reiboldt, PA. Messina, M. Iqbal, J. Singh, ER. Bacon, TS. Angeles, SX. Yang, MS. Albom, C. Robinson, H. Chang, BA. Ruggeri, JP. Mallamo, Structure-guided identification of novel VEGFR-2 kinase inhibitors via solution phase parallel synthesis, Bioorg. Med. Chem. Lett., 16 (2006).

T. Ratan Bal, B. Anand, P. Yogeeswari, DH. Sriram, Synthesis and evaluation of anti-HIV activity of isatin β-thiosemicarbazone derivatives, Bioorg. Med. Chem. Lett. 15 (2005) 4451- 4455.

G. Cecile, D. Douguet, V. Huteau, M. Gilles, ML. Helene, P. Sylvie, Substituted benzylpyrimidines targeting thymidine monophosphate kinase of Mycobacterium tuberculosis: synthesis and in vitro anti-mycobacterial activity, Bioorg. Med. Chem. 16 (2008).

R. Lin, G. Sigmond, PJ. Johnson, SK. Connolly, E. Wetter, TV. Binnun, WV. Hughes, NB. Murray, SJ. Pandey, MM. Mazza, AR. Adams, F. Pesquera, AM. Steven, Synthesis and evaluation of 2, 7-diamino-thiazolo [4, 5-d] pyrimidine analogues as anti-tumor epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors, Bioorg. Med. Chem. Lett., 19 (2009).

(a) Q. Chen, X. Zhu, L. Jiang, LM. Yang, G. Fu, Synthesis, antifungal activity and CoMFA analysis of novel 1, 2, 4-triazolo [1, 5-a] pyrimidine derivatives, Eur. J. Med. Chem., 43 (2008).

MA. Borad, MN. Bhoi, NP. Prajapati, HD. Patel, A Review on Synthesis of Spiro Heterocyclic Compounds from Isatin, Synth. Commun., 44 (2014) 897-922.

MA. Borad, MN. Bhoi, NP. Prajapati, HD. Patel, A Review on Synthesis of multi Spiro Heterocyclic Compounds from Isatin, Synth. Commun., 44, (2014) 1-15.

MA. Borad, MN. Bhoi, DP. Rajani, SD. Rajani, HD. Patel, synthesis and antimicrobial activities of 2-(4-substituted phenyl)-1, 10b dihydrospiro[benzo[e]pyrazolo[1, 5-c][1, 3]oxaz ine5, 3'-indolin]-2'-one derivative from isatin, WJPPS, 3 (2014).

A. Agarwal, R. Ashutosh, N. Goyal, MS. Chauhana, S. Gupta, Dihydropyrido [2, 3-d] pyrimidines as a new class of antileishmanial agents, Bioorg. Med. Chem. 13 (2005) 66786684.

Show More Hide

Cited By:

[1] M. Bhoi, M. Borad, E. Pithawala, H. Patel, "Novel benzothiazole containing 4H-pyrimido[2,1-b]benzothiazoles derivatives: One pot, solvent-free microwave assisted synthesis and their biological evaluation", Arabian Journal of Chemistry, 2016

DOI: https://doi.org/10.1016/j.arabjc.2016.01.012

[2] M. Borad, M. Bhoi, S. Rathwa, M. Vasava, H. Patel, C. Patel, H. Pandya, E. Pithawala, J. Georrge, "Microwave-Assisted ZrSiO2 Catalysed Synthesis, Characterization and Computational Study of Novel Spiro[Indole-Thiazolidines] Derivatives as Anti-tubercular Agents", Interdisciplinary Sciences: Computational Life Sciences, 2016

DOI: https://doi.org/10.1007/s12539-016-0195-2

[3] M. Taha, M. Arbin, N. Ahmat, S. Imran, F. Rahim, "Synthesis: Small library of hybrid scaffolds of benzothiazole having hydrazone and evaluation of their β -glucuronidase activity", Bioorganic Chemistry, Vol. 77, p. 47, 2018

DOI: https://doi.org/10.1016/j.bioorg.2018.01.002