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Volume: 9, Issue: 7, July, 2019
Synthesis, in silico study and in vitro anti-microbial evaluation of some new N-benzoyl-N'-[2-(4-chloro-phenoxy)-acetyl]-hydrazides analogsAuthor Affiliations
In bacterial resistance duty, the prompt increase against existent anti-microbial drugs is a challenging universal health problem. Bacteria represent a highly significant threat globally to healthcare-associated infections, also responsible for the majority of hospital infections, which leads to an increase in the mortality and burden of worldwide healthcare duty. In this investigation, we reported the synthesis novel substitutes of phenoxy hydrazide analogs (6a–f) and have been screened for in vitro anti-bacterial and anti-fungal activities to determine the inhibition zone by using the paper disk agar diffusion technique and broth dilution to evaluate the minimum inhibitory concentration values. The structure–activity relationship suggest that among the series (6a–f), compounds (6e) with two chloro groups and (6f) with four fluoro groups showed good inhibition against pathogenic microbes. Furthermore, these results were also confirmed by the in silico study. Based on this studies, there are a scopes of developing compounds (6e) and (6f) into potent anti-microbial drugs in the near future.
Copyright: The Author(s). This is an open access article distributed under the Creative Commons Attribution Non-Commercial License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Al-Ostoot FH, Vidya R, Mohammed YH, Jyothi M, Pallavi HM, Khanum SA. Statistical analysis of antimicrobial data of 2-[2-(Aroyl) aroyloxy] methyl1, 3, 4 Oxadiazoles analogues using ANOVA. Asian J Res Chem, 2018; 11(2):293-7. https://doi.org/10.5958/0974-4150.2018.00055.X
Arias CA, Murray BE. Antibiotic-resistant bugs in the 21st century-a clinical super-challenge. N Engl J Med, 2009; 360(5):439-43. https://doi.org/10.1056/NEJMp0804651
Backes GL, Neumann DM, Jursic BS. Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides. Bioorgan Med Chem, 2014; 22(17):4629-36. https://doi.org/10.1016/j.bmc.2014.07.022
Bär F, Hopf H, Knorr M, Krahl J. Rancimat and PetroOxy oxidation stability measurements of rapeseed oil methyl ester stabilized with hydrazides and antioxidants. Fuel, 2018; 232:108-13. https://doi.org/10.1016/j.fuel.2018.05.095
Bordoloi M, Kotoky R, Mahanta JJ, Sarma TC, Kanjilal PB. Anti-genotoxic hydrazide from Crinum defixum. Eur J Med Chem, 2009; 44(6):2754-7. https://doi.org/10.1016/j.ejmech.2008.09.041
Dhami NK, Reddy MS, Mukherjee A. Application of calcifying bacteria for remediation of stones and cultural heritages. Front Microbiol, 2014; 5:304. https://doi.org/10.3389/fmicb.2014.00304
Geetha DV, Al-Ostoot FH, Mohammed YH, Sridhar MA, Khanum SA, Lokanath NK. Synthesis, Elucidation, Hirshfeld surface analysis, and DFT calculations of 4-chloro-N-[2-(2-1H-indol-3-yl-acetylamino)-phenyl]-benzamide. J Mol Struct, 2019; 1178:384-93. https://doi.org/10.1016/j.molstruc.2018.10.016
Gholivand K, Hosseini Z, Farshadian S, Naderi-Manesh H. Synthesis, characterization, oxidative degradation, antibacterial activity and acetylcholinesterase /butyrylcholin esterase inhibitory effects of some new phosphorus (V) hydrazides. Eur J Med Chem, 2010; 45(11):5130-9. https://doi.org/10.1016/j.ejmech.2010.08.025
Harrison JW, Svec TA. The beginning of the end of the antibiotic era? Part I. The problem: abuse of the "miracle drugs". Quintessence Int, 1998; 29(3).
Khanum SA, Khanum NF, Shashikanth M. Synthesis and anti-inflammatory activity of 2-aryloxy methyl oxazolines. Bioorgan Med Chem Lett, 2008; 18(16):4597-601. https://doi.org/10.1016/j.bmcl.2008.07.029
Khanum SA, Shashikanth S, Sudha BS. A facile synthesis and antimicrobial activity of 3-(2-aroylaryloxy) methyl-5-mercapto-4-phenyl- 4H-1, 2, 4-triazole and 2-(2-aroylaryloxy) methyl-5-N-phenylamino-1, 3, 4-thiadiazole analogues. Sci Asia, 2003; 34:383-92. https://doi.org/10.2306/scienceasia1513-1874.2003.29.383
Kim M, Lee S, Park EB, Kim KJ, Lee HH, Shin JS, Fischer K, Koeberle A, Werz O, Lee KT, Lee JY. Hit-to-lead optimization of phenylsulfonyl hydrazides for a potent suppressor of PGE2 production: synthesis, biological activity, and molecular docking study. Bioorgan Med Chem Lett, 2016; 26(1):94-9. https://doi.org/10.1016/j.bmcl.2015.11.024
Kumar SM, Hezam AO, Manjunath BC, Shamprasad VR, Mohammed YH, Mahesh N, Shaukath AK, Lokanath NK, Byrappa K. Crystal packing analysis of 1-(3, 4-dimethoxyphenyl)-3-(4-bromophenyl) prop-2-en-1-one exhibiting a putative halogen bond CBr O. J Mol Struct, 2018a; 1156:216-23. https://doi.org/10.1016/j.molstruc.2017.11.094
Kumar SM, Manjunath BC, Al-Ostoot FH, Jyothi M, Al- Ghorbani M, Khanum SA, Kudva AK, Lokanath NK, Byrappa K. Synthesis, crystal structure and Hirshfeld surfaces of 1-(3, 4-dimethoxyphenyl)-3-(3- hydroxyphenyl) prop 2-en-1-one. Chem Data Collect, 2018b; 15:153-60. https://doi.org/10.1016/j.cdc.2018.05.003
Kumara K, Al-Ostoot FH, Mohammed YH, Khanum SA, Lokanath NK. Synthesis, crystal structure and 3D energy frameworks of ethyl 2-[5-nitro-2-oxopyridine-1 (2H)-yl] acetate: Hirshfeld surface analysis and DFT calculations. Chem Data Collect, 2019; 6:100195. https://doi.org/10.1016/j.cdc.2019.100195
Mimica-Dukić N, Kujundžić S, Soković M, Couladis M. Essential oil composition and antifungal activity of Foeniculum vulgare
Mill. obtained by different distillation conditions. Phytother Res, 2003; 17(4):368-71. https://doi.org/10.1002/ptr.1159
Mohammed YH, Khanum SA. The critical role of novel benzophenone analogs on tumor growth inhibition targeting angiogenesis and apoptosis. MedChemComm, 2018; 9(4):639-56. https://doi.org/10.1039/C7MD00593H
Mohammed YH, Malojirao VH, Thirusangu P, Al-Ghorbani M, Prabhakar BT, Khanum SA. The Novel 4-Phenyl-2-Phenoxyacetamide Thiazoles modulates the tumor hypoxia leading to the crackdown of neoangiogenesis and evoking the cell death. Eur J Med Chem, 2018; 143:1826-39. https://doi.org/10.1016/j.ejmech.2017.10.082
Mohammed YH, Thirusangu P, Vigneshwaran V, Prabhakar BT, Khanum SA. The anti-invasive role of novel synthesized pyridazine hydrazide appended phenoxy acetic acid against neoplastic development targeting matrix metallo proteases. Biomed Pharmacother, 2017; 95:375-86. https://doi.org/10.1016/j.biopha.2017.08.105
Morjan RY, Mkadmh AM, Beadham I, Elmanama AA, Mattar MR, Raftery J, Pritchard RG, Awadallah AM, Gardiner JM. Antibacterial activities of novel nicotinic acid hydrazides and their conversion into N-acetyl-1, 3, 4-oxadiazoles. Bioorgan Med Chem Lett, 2014; 24(24):5796- 800. https://doi.org/10.1016/j.bmcl.2014.10.029
Nwakanma C, Njoku EN, Pharamat T. Antimicrobial activity of secondary metabolites of fungi isolated from leaves of bush mango. Next Generat Sequenc Appl, 2016; 3:135. https://doi.org/10.4172/2469-9853.1000135
Omar K, Geronikaki A, Zoumpoulakis P, Camoutsis C, Soković M, Ćirić A, Glamočlija J. Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorgan Med Chem, 2010; 18(1):426- 32. https://doi.org/10.1016/j.bmc.2009.10.041
Ozdemir UO, Ilbiz F, Gunduzalp AB, Ozbek N, Genç ZK, Hamurcu F, Tekin S. Alkyl sulfonic acide hydrazides: synthesis, characterization, computational studies and anticancer, antibacterial, anticarbonic anhydrase II (hCA II) activities. J Mol Struct, 2015; 1100:464- 74. https://doi.org/10.1016/j.molstruc.2015.07.054
Perron GG, Kryazhimskiy S, Rice DP, Buckling A. Multidrug therapy and evolution of antibiotic resistance: when order matters. Appl Environ Microbiol, 2012; 78(17):6137-42. https://doi.org/10.1128/AEM.01078-12
Prashanth T, Ranganatha VL, Naveen P, Gurupadaswamy HD, Begum AB, Al-Ghorbani M, Khanum SA. Synthesis of (4-benzoyl-phenoxy)-acetic acid derivatives and their efficacy as antioxidant agents. Free Radicals Antioxidants, 2013; 3:S50-54. https://doi.org/10.1016/j.fra.2013.09.002
Puttaswamy N, Malojiao VH, Mohammed YH, Sherapura A, Prabhakar BT, Khanum SA. Synthesis and amelioration of inflammatory paw edema by novel benzophenone appended oxadiazole derivatives by exhibiting cyclooxygenase-2 antagonist activity. Biomed Pharmacother, 2018; 103:1446-55. https://doi.org/10.1016/j.biopha.2018.04.167
Sen A, Batra A. Evaluation of antimicrobial activity of different solvent extracts of medicinal plant: Melia azedarach L. Int J Curr Pharm Res, 2012; 4(2):67-73.
Sheykhi-Estalkhjani A, Mahmoodi NO, Yahyazadeh A, Nadamani MP. Synthesis of new bis-benzylidene-hydrazides as a sensitive chromogenic sensor for naked-eye detection of CN¯ and AcO¯ ions. Tetrahedron, 2018; 74(37):4868-74. https://doi.org/10.1016/j.tet.2018.07.050
Sokovic M, Marin PD, Brkic D, van Griensven LJ. Chemical composition and antibacterial activity of essential oils against human pathogenic bacteria. Food 2008; 1(2):220-6.
Spellberg B, Guidos R, Gilbert D, Bradley J, Boucher HW, Scheld WM, Bartlett JG, Edwards J Jr; Infectious Diseases Society of America. The epidemic of antibiotic-resistant infections: a call to action for the medical community from the Infectious Diseases Society of America. Clin Infect Dis, 2008; 46(2):155-64. https://doi.org/10.1086/524891
Vaikunthanathan T, Safinia N, Lombardi G, Lechler RI. Microbiota, immunity and the liver. Immunol Lett, 2016; 171:36-49. https://doi.org/10.1016/j.imlet.2016.01.008
Velezheva V, Brennan P, Ivanov P, Kornienko A, Lyubimov S, Kazarian K, Nikonenko B, Majorov K, Apt A. Synthesis and antituberculosis activity of indole-pyridine derived hydrazides, hydrazide-hydrazones, and thiosemicarbazones. Bioorgan Med Chem Lett, 2016; 26(3):978-85. https://doi.org/10.1016/j.bmcl.2015.12.049
Yang L, Wang P, Wu JF, Yang LM, Wang RR, Pang W, Li YG, Shen YM, Zheng YT, Li X. Design, synthesis and anti-HIV-1 evaluation of hydrazide-based peptidomimetics as selective gelatinase inhibitors. Bioorgan Med Chem, 2016; 24(9):2125-36. https://doi.org/10.1016/j.bmc.2016.03.043
Yehia AT, Alzowahi FA, Kadam TA, Shaikh RU. In vitro evaluation of antimicrobial and antioxidant activity of Dragon's blood tree (Dracaena cinnabari Balf. f.) of Socotra Island (Yemen). J Coastal Life Med, 2013; 1(2):123-9.
Zabiulla, Neralagundi HS, Begum AB, Prabhakar BT, Khanum SA. Design and synthesis of diamide-coupled benzophenones as potential anticancer agents. Eur J Med Chem, 2016; 115:342-51. https://doi.org/10.1016/j.ejmech.2016.03.040