SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF INDOLE DERIVATIVES BEARING BENZIMIDAZOLE/BENZOTHIAZOLE MOIETY


Basavaraj Shivabasappa Naraboli, Jayaprakash Sharanappa Biradar

Abstract


Objective: The present work deals with the synthesis and characterization of biologically active new indole derivatives viz., 2-((1H-benzo[d]imidazol-2-yl)thio)-N-(4-(3-(1H-indol-3-yl)acryloyl)phenyl)acetamide 6a-d, N-(4-(3-(1H-indol-3-yl)acryloyl)phenyl)-2-((5-methoxy-1H-benzo[d]imidazol-2-yl)thio)acetamide 7a-d and N-(4-(3-(1H-indol-3-yl)acryloyl)phenyl)-2-(benzo[d]thiazol-2-ylthio)acetamide 8a-d.

Methods: All these newly synthesized compounds were screened for their in vitro antimicrobial activity by an agar plate diffusion method, antioxidant activities: like 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging activity (RSA), ferric ions (Fe3+) reducing antioxidant power (FRAP), ferrous (Fe2+) metal ion chelating activity.

Results: The structures of all the newly synthesized compounds were characterized by their IR, 1HNMR, mass spectral studies and elemental analysis. Compounds 6b, 7a, 7b, 8a and 8b exhibited good radical scavenging activity (RSA) at a concentration 100 µg/ml, compounds 7b, 7c, 7d and 8b displayed good ferric ions (Fe3+) reducing antioxidant power (FRAP) at a concentration 100 µg/ml, compounds 7b, 7d, 8b and 8d showed good ferrous (Fe2+) ion metal chelating activity. Compounds 7d and 8d exhibited good activity against all the screened bacteria and fungi.

Conclusion: The synthesised compounds 7d having methoxy group at 5 positions of benzimidazoles ring, bromo group at 5 positions of indole ring, and 8d having bromo group at position 5 of indole ring, both the compounds have exhibited potent antimicrobial activity. Some compounds have shown very good antioxidant activity.


Keywords


Indole, Benzimidazole, Benzothiazole, Antimicrobial, Antioxidant

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References


Stansfield I, Pompei M, Conte I, Ercolani C, Migliaccio G, Jairaj M, et al. Development of carboxylic acid replacements in indole-N-acetamide inhibitors of hepatitis C virus NS5B polymerase. Bioorg Med Chem Lett 2007;17:5143-9.

Li YY, Wu HS, Tang L, Feng CR, Yu JH, Li Y, et al. The potential insulin sensitizing and glucose lowering effects of a novel indole derivative in vitro and in vivo. Pharmcol Res 2007;56:335-43.

RJ Sundberg. The Chemistry of Indoles. New York: Academic Press; 1996.

Mezencev R, Kutschy P, Salayova A, Updegrove T, McDonald JF. The design, synthesis and anticancer activity of new nitrogen mustard derivatives of natural indole phytoalexin 1-methoxyspirobrassinol. Neoplasma 2009;56:321-30.

Mardia TEl Sayed, Nehal A Hamdy, Dalia A Osman, Khadiga M Ahmed. Indoles as anti-cancer agents. Adv Mod Oncol Res 2015;1:20–35.

Biradar JS, Sasidhar BS, Parveen R. Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives. Eur J Med Chem 2010;45:4074–8.

Biradar JS, Somappa SB. Synthesis of novel Indolyl benzo[b][1,4]diazepins as a potent antimicrobial and antioxidant agents. Arab J Chem 2016;9(S2):S1063-S1068.

Guerra AS, Malta DJ, Laranjeira LP, Maia MB, Colaço NC, de Lima Mdo C, et al. Anti-inflammatory and antinociceptive activities of indole-imidazolidine derivatives. Int Immuno-pharmacol 2011;11:1816-22.

Vibha C Patil, Kishore P Bhusari, Pramod B Khedekar. Synthesis and anti-inflammatory activity of some 3-substituted thiazolyl and oxazolyl indole derivatives. World J Pharm Pharma Sci 2014;3:1292-306.

Ming-Zhi Zhang, Qiong Chen, Guang-Fu Yang. A review on recent developments of indole-containing antiviral agents. Eur J Med Chem 2015;89:421-41.

Saravanan B, Akhilesh Upgade, Anusha Bhaskar, Manivannan V. Synthesis and molecular docking studies of diethyl 2-{[3-(2,4,6-trimethyl benzyl)-1-phenylsulfonyl-1h-indol-2-yl]methyl-idene} propanedioate against hypertensive protein as a potential target. Asian J Pharm Clin Res 2013;6:172-4.

P Lavanya, M Suresh, Y Kotaiah, N Harikrishna, C Venkata Rao. Synthesis, antibacterial, antifungal and antioxidant activity studies on 6-bromo-2-substituted phenyl-1H-imidazo [4, 5-b] pyridine. Asian J Pharm Clin Res 2011;4:69-73.

Gaozhi Chen, Zhiguo Liu, Yali Zhang, Xiaoou Shan, Lili Jiang, Yunjie Zhao, et al. Synthesis and anti-inflammatory evaluation of novel benzimidazole and imidazopyridine derivatives. ACS Med Chem Lett 2013;4:69–74.

Y Radha, A manjula, B Madhava Reddy, B Vittal Rao. Synthesis and biological activity of novel benzimidazoles. Indian J Chem 2011. p. 1762-73.

Mi Kyoung Kim, Heerim Shin, Kwang-su Park, Hyungmi Kim, Jiseon Park, Kangjeon Kim. Benzimidazole derivatives as potent JAK1-selective inhibitors. J Med Chem 2015;58:7596–602.

Vivek K Vyas, Manjunath Ghate. QSAR modelling of substituted benzimidazole derivative as angiotensin II-AT1 receptor antagonist: WHIM descriptors. Int J Drug Des Discovery 2011;1:375-82.

Tonelli M, Simone M, Tasso B, Novelli F, Boido V, Sparatore F, et al. Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenyl benzimidazole derivatives. Bioorg Med Chem 2010;18:2937-53.

Shingalapur RV, Hosamani KM, Keri RS, Hugar MH. Derivatives of benzimidazole pharmacophore: synthesis, anticonvulsant, antidiabetic and DNA cleavage studies. Eur J Med Chem 2010;45:1753-9.

Ramanatham Vinodkumar, Sanjay Dashrath Vaidya, Bobba Venkata Siva Kumar, Umesh Nanasaheb Bhise, Shekhar Bhaskar Bhirud, Uday Chandrakant Mashelkar. Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted-2-(4-phenylethynyl-phenyl)-1H-benzimidazoles and N-substituted 2[4-(4,4-dimethyl-thiochroman-6-yl-ethynyl)-phenyl)-1H-benz-imidazoles. Eur J Med Chem 2008;43:986–95.

Suresh Maddila, Sridevi Gorle, Nuthangi Seshadri, Palakondu Lavanya, Sreekanth, B Jonnalagadda. Synthesis, antibacterial and antifungal activity of novel benzothiazole pyrimidine derivatives. Arab J Chem 2016;9:681–7.

Jitender K Malik, Himesh Soni, AK Singhai. Synthesis, characterization and evaluation for antifungal activity of substituted diaryl imidazo [2, 1, b]-benzothiazole. J Pharma Res 2013; 7:39–46.

Bhupendra Mistry, Rahul V Patel, Young Soo Keum, Doo Hwan Kim. Evaluation of the biological potencies of newly synthesized berberine derivatives bearing benzothiazole moieties with substituted functionalities. J Saudi Chem Soc 2017;21:210–9.

Rupali Likhar, P Perumal, Nitin Kolhe, VH Bhaskar, Pratibha Daroi. Synthesis and antioxidant activity of novel 2-aryl substituted benzothiazole derivatives. Int J Curr Pharm Res 2015;7:34-7.

AV Subba Rao, Konderu Swapna, Siddiq Pasha Shaik, V Lakshma Nayak, T Srinivasa Reddy, Satish Sunkari, et al. Synthesis and biological evaluation of cis-restricted triazole/tetrazole mimics of combretastatin benzothiazole hybrids as tubulin polymerization inhibitors and apoptosis inducers. Bioorg Med Chem 2017;25:977-99.

Kalpesh Parikh, Deepkumar Joshi. Antibacterial and antifungal screening of newly synthesized benzimidazole-clubbed chalcone derivatives. Med Chem Res 2013;22:3688–97.

Hatano T, Kangawa H, Yasuhara T, Okuda T. Two new favonoids and other constituents in licorice root: their relative astringency and radical scavenging effects. Chem Pharm Bull 1988;36:2090–7.

Oyaizu M. Antioxidative activity of browning substances on glucosamine. Japan Nutr 1986;44:307–15.

Dinis TCP, Maderia VMC, Almeida LM. Action of phenolic derivatives (acetoaminophen, salycilate, and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as proxy radical scavengers. Arch Biochem Biophys 1994;315:161–9.

Saundane AR, Prabhaker W. Synthesis, Antioxidant, Antimicrobial, Antimycobacterial, and Cytotoxic Activities of Azetidinone and Thiazolidinone Moieties Linked to Indole Nucleus. J Chem 2013. http://dx.doi.org/10.1155/ 2013/ 543815.




About this article

Title

SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF INDOLE DERIVATIVES BEARING BENZIMIDAZOLE/BENZOTHIAZOLE MOIETY

Keywords

Indole, Benzimidazole, Benzothiazole, Antimicrobial, Antioxidant

DOI

10.22159/ijpps.2017v9i8.19725

Date

01-08-2017

Additional Links

Manuscript Submission

Journal

International Journal of Pharmacy and Pharmaceutical Sciences
Vol 9, Issue 8, 2017 Page: 128-138

Online ISSN

0975-1491

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44 Views | 73 Downloads

Authors & Affiliations

Basavaraj Shivabasappa Naraboli
Department of Studies and Research in Chemistry, Gulbarga University, Kalaburagi 585106, Karnataka, INDIA
India

Jayaprakash Sharanappa Biradar
Department of Studies and Research in Chemistry, Gulbarga University, Kalaburagi 585106, Karnataka, INDIA
India


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