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An efficient protocol for the synthesis of novel 2-amino-N'-(1-(aryl-2-oxo-2Hchromen-3-yl)ethylidene) benzohydrazides act as an antimicrobial agents

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We report here the protocol for the preparation of 2-amino-N'-(1-(aryl-2-oxo-2H-chromen-3-yl)ethylidene)benzohydrazides compounds in moderate to excellent yields (46–86%) within a short reaction time (10–15 min), through a clean and efficient procedure. Additionally, the method has a wide substrate scope and provides an accessible route for the large-scale direct synthesis of 2-amino-N'-(1-(aryl-2-oxo-2H-chromen-3-yl)ethylidene)benzohydrazides. The products were assayed for their in vitro biological assay antimicrobial evaluation against two Gram-negative bacteria Escherichia coli MTCC 442, Pseudomonas aeruginosa MTCC 441 and antifungal activity against Candida albicans MTCC 227, Aspergillus Niger MTCC 282, Aspergillus clavatus MTCC 1323 at different concentrations which compared with ampicillin, chloramphenicol, ciprofloxacin, norfloxacin, nystatin, and greseofulvin in as standard drugs which are presented.
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  • Department of Home Science, Saurashtra University, Rajkot - 360005, Gujarat, India
  • Department of Home Science, Saurashtra University, Rajkot - 360005, Gujarat, India
  • [1] Mantovani, P. Allavena, A. Sica, Cancer-related inflammation. Nature 454 (2008) 436-444
  • [2] R. S. Chavan, H. N. More, A.V. Bhosale, Synthesis and evaluation of analgesic and anti-inflammatory activities of a novel series of 3-(4, 5-dihydropyrazolyl)-indoles, International Journal of Pharmacuetical and Biomedical Research, 1(4) (2010) 135-143
  • [3] S. Rajasekaran., G. K. Rao, S. P. N. Pai, A. Ranjan, Synthesis of novel coumarin derivatives and its biological evaluations, International journal of chem tech research, 3(2) (2011) 555-559
  • [4] S. D .Nachiket, R. P. Shashikant, S. S. Dengale, D. S. Musmade, M. Shelar, V. Tambe, M. Hole, Pharmacological review on natural antidiarrhoel agents, Der Pharma Chemica, 2(2) (2010) 65-71
  • [5] A. O. Olayinka, N. C. Obinna, Microwave‐assisted synthesis and evaluation of antimicrobial activity of 3‐{3‐(s‐aryl and s‐heteroaromatic)acryloyl}‐2H‐chromen‐2‐one derivatives, Journal of Heterocyclic Chemistry, 47 (2010) 179-187
  • [6] D. I. Brahnbhatt, J. M. Gajera, V. P. Pandya, M. A. Patel, Synthesis of 3-(6-aryl-pyridin-2-yl)-and 8-(6-aryl-pyridin-2-yl) coumarins, Ind. J. Chem. 46(B) (2007) 869-871
  • [7] R. Sharma, V. Arya, A review on fruits having anti-diabetic potential. Journal of Chemical and Pharmaceutical Research, J. Chem. Pharm. Res. 3(2) (2011) 204-212.
  • [8] R. D. H. Murrey, D. Medez, S. A. Brown, The Natural Coumarins: Occurrence, Chemistry, and Biochemistry, John Wiley Interscience, New York (1982).
  • [9] S. R. Ghantwal, S. D. Samant, Claisen rearrangement of 3-bromo-, 3, 6-dibromo-, 3, 8-dibromo-and 8-iodo/aminomethyl/acetyl-7-allyloxy-4-methylcoumarins, Ind. J. Chem. 38(B) (1999) 1242-1247
  • [10] P. L. Majumder, S. Majumder, Enzyme inhibitory activities an insight into the structure–Activity relationship of biscoumarin derivatives, Eur. J. Med. Chem. 28 (1993) 572-578
  • [11] K. K. Upadhyay, R. K. Mishra, A. Kumar, A convenient synthesis of some coumarin derivatives using SnCl2· 2H2O as catalyst, Catal. Lett. 121 (2008) 118-120
  • [12] T. Harayama, K. Nakatsuka, H. Nishioka, K. Murakami, N. Hayashida, H. Ishii, Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent. II: Synthesis of Bromo-and Methoxycarbonylcoumarins, Chem. Pharm. Bull. 42(10) (1994) 2170-2173
  • [13] A. Shaabani, R. Ghadari, A. Rahmati, A. H. Rezayan, Coumarin synthesis via Knoevenagel condensation reaction in 1, 1, 3, 3-N, N, N′, N′-tetramethylguanidinium trifluoroacetate ionic liquid, J. Iran Chem. Soc. 6(4) (2009) 710-14
  • [14] D. H. More, P. P. Mahulikar, Microwave assisted one-pot synthesis of nitrogen and oxygen containing heterocycles from acyl meldrum’s acid, Indian Journal of Chemistry, 50(B) (2011) 745- 747
  • [15] M. Khadijah, A. Zaydi, Microwave assisted synthesis, part 1: rapid solventless synthesis of 3-substituted coumarins and benzocoumarins by microwave irradiation of the corresponding enaminones, Molecules, 8 (2003) 541-555
  • [16] Z. Hua, J. Geo, L. Zhu-bo, M. Bu-Hyun, S. D. Soo, G. Manjunath, A comparative study of microwave assisted and conventional synthesis of 2,3-dihydro-2-aryl-4-[4-(2–oxo–2H–chromen–3–yl)–1,3-thiazol–2–ylamino]-1,5–benzothiazepines and its antimicrobial activity, Arkivoc, (2008) 233-244
  • [17] F. Zoni, P. Vicini, Zoni, F., & Vicini, P. (1998). Antimicrobial activity of some 1, 2-benzisothiazoles have a benzenesulfonamides moiety, Arch. Pharm. 331 (1998) 219
  • [18] H. Yoshino, N. Ueda, J. Niijima, H. Sugumi, Y. Kotake, N. Koyanagi, K. Yoshimatsu, M. Asada, T. Watanabe, T. Nagasu, K. Tsutahara, A. Lijima, K. Kitoh, Synthesis of novel coumarin derivatives and its biological evaluations, J. Med. Chem. 35 (1992) 2496
  • [19] A. Vogel; Preparation of benzoic acid from Tonka beans and from the flowers of Melilot or sweet clover, Annalen der Physik, 64 (1820) 161-166
  • [20] S. Sethna; N. Shah, The Chemistry of Coumarins Chem. Re. 36 (1945) 112.
  • [21] Kostova; S. Raleva; P. Genova; R. Argirova, Structure-activity relationships of synthetic coumarins as HIV-1 inhibitors, Bioinorg. Chem. Appl. 1 (2006) 68274–68279
  • [22] R.P. Bhole, K.P. Bhusari, Synthesis, antihypertensive activity, and 3D-QSAR studies of some new p-hydroxybenzohydrazide derivatives, Arch. Pharm. (Weinheim), 344 (2011) 119-134
  • [23] X. Zhong, H.L. Wei, W.S. Liu, D.Q. Wang, X. Wang, The crystal structures of copper(II), manganese(II), and nickel(II) complexes of a (Z)-2-hydroxy-N'-(2- oxoindolin-3-ylidene) benzohydrazide–potential antitumor agents, Bioorg. Med. Chem. Lett 17 (2007) 3774-3777
  • [24] D. Liu, Z. Chen, S. Qin, W. Huang, L. Jiang, F. Liang, Synthesis, characterization, and properties of four metal complexes with mulitdentate N-acyl-salicylhydrazide ligands, Z. An org. Allg. Chem. 637 (2011) 1401-1408
  • [25] R. P. Bhole, D.D. Borkar, K.P. Bhusari, P.A. Patil, Design and synthesis of phydroxybenzohydrazide derivatives for their antimycobacterial activity, J. Korean Chem. Soc. 56 (2012) 236-245
  • [26] A. A. Alhadi, R. Othman, W.A. Yehye, N.A. Rahman, Formation of 1,3,4-oxadiazolines and 1,3,4-oxadiazepines through acetylation of salicylic hydrazones, Tetrahedron Lett. 56 (2015) 573-576
  • [27] Y.-H. Jiang, C.-G. Yan, Indium chloride catalyzed three-component reaction for the synthesis of 2-((oxoindolin-3-yl)-4,5,6,7-tetrahydro-1H-indol-1-yl)benzamides, RSC Adv. 6 (2016) 42173-42179
  • [28] E. M. Sarshira, N.M. Hamada, Y. M. Moghazi, M. M. Abdelrahman, Synthesis and biological evaluation of some heterocyclic compounds from salicylic acid hydrazide, J. Heterocycl. Chem. 53 (2016) 1970-1982
  • [29] H. Truong, Nguyen, D. K. Nguyen Chau, P. H. Tran, A green and efficient method for the synthesis of pyrroles using a deep eutectic solvent ([CholineCl][ZnCl2]3) under solvent-free sonication, New J. Chem. 41 (2017) 12481-12489
  • [30] E.M. Sarshira, N.M. Hamada, Y.M. Moghazi, M.M. Abdelrahman, Synthesis and biological evaluation of some heterocyclic compounds from salicylic acid hydrazide, J. Heterocycl. Chem. 53 (2016) 1970-1982
  • [31] Nguyen Tien, T. Nguyen Van, G. Le Duc, M. Vu Quoc, T. Vu Quoc, T. Pham Chien, H. Nguyen Huy, A. Dang Thi Tuyet, T. Nguyen Van, L. Van Meervelt, Synthesis, structure and in vitro cytotoxicity testing of some 1,3,4-oxadiazoline derivatives from 2-hydroxy-5-iodobenzoic acid, Acta. Crystallogr. C Struct. Chem. 74 (2018) 839-846
  • [32] National Committee for Clinical and Laboratory Standards, Method for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically Approved Standard, fourth ed. NCCLS, Villanova, Italy, Document M 100-S7 (1997) S100-S157
  • [33] H. D. Isenberg, Essential Procedures for Clinical Microbiology, ASM Press, (1998).
  • [34] J. Zgoda, J. Porter, Pharmaceutical Biology, 39 (2001) 221-225
  • [35] W. O. Foye, T. L. Lemke, D. A. Williams, Principles of medicinal chemistry. 4th Edn. B. I. Waverly Pvt Ltd, New Delhi, 768-769 (1995) 806-811
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