Characterisation of twelve newly synthesised N-(substituted phenyl)-2-chloroacetamides with QSAR analysis and antimicrobial activity tests

1Apostolov S, Vaštag Đ, Matijević B, Nakomčić J, Marinković A. Studing retention behavior lipophilicity and pharmacokinetic characteristics of N-substituted Phenyl-2-chloroacetamides. Contemp Mater 2014;1:101–10. doi: 10.7251/cm.v1i5.1505Apostolov S Vaštag Đ Matijević B Nakomčić J Marinković A Studing retention behavior lipophilicity and pharmacokinetic characteristics of N-substituted Phenyl-2-chloroacetamides Contemp Mater 20141101 10 10.7251/cm.v1i5.1505Open DOISearch in Google Scholar

2Berest G. Synthesis and biological activity of novel N-cycloalkyl-(cycloalkylaryl)-2-[(3-R-2oxo-2H-[1,2,4] triazino[2,3-C]quinazoline-6-yl)thio]acetamides. Eur J Med Chem 2011;46:6066–74. doi: 10.1016/j.ejmech.2011.10.022Berest G Synthesis and biological activity of novel N-cycloalkyl-(cycloalkylaryl)-2-[(3-R-2oxo-2H-[1,2,4] triazino[2,3-C]quinazoline-6-yl)thio]acetamides Eur J Med Chem 2011466066 74 10.1016/j.ejmech.2011.10.02222051065Open DOISearch in Google Scholar

3Vastag G, Apostolov S, Matijević B. Prediction of lipophilicity and pharmacokinetics of chloroacetamides by chemometric approach. Iran J Pharm Res 2018;17:100–14. doi: 10.22037/IJPR.2018.2177Vastag G Apostolov S Matijević B Prediction of lipophilicity and pharmacokinetics of chloroacetamides by chemometric approach Iran J Pharm Res 201817100 14 10.22037/IJPR.2018.2177Open DOISearch in Google Scholar

4Özkay D, Özkay U, Can Y, Özgür D. Synthesis and analgesic effects of 2-(2-carboxyphenylsulfanyl)-N-(4-substitutedphenyl)acetamide derivatives. Med Chem Res 2011;20:152–7. doi: 10.1007/s00044-010-9300-yÖzkay D Özkay U Can Y Özgür D Synthesis and analgesic effects of 2-(2-carboxyphenylsulfanyl)-N-(4-substitutedphenyl)acetamide derivatives Med Chem Res 201120152 7 10.1007/s00044-010-9300-yOpen DOISearch in Google Scholar

5Ertan T. Synthesis and biological evaluation of new N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamides and phenylacetamides as antimicrobial agents. Bioorg Med Chem 2007;15:2032–44. doi: 10.1016/j.bmc.2006.12.035Ertan T Synthesis and biological evaluation of new N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamides and phenylacetamides as antimicrobial agents Bioorg Med Chem 2007152032 44 10.1016/j.bmc.2006.12.03517223562Open DOISearch in Google Scholar

6Hayakawa M. Phenylacetamide derivative. US Patent Application Publication Pub. No.: 20100286171 A1 (2010) [displayed 11 February 2021]. Available at https:// p a ten t i m a g e s. s to r a g e. go ogle a pi s. co m / d0/4d/69/2960cd9f20dc88/US20100286171A1.pdfHayakawa M Phenylacetamide derivative. US Patent Application Publication Pub. No.: 20100286171 A1 2010 [displayed 11 February 2021] Available at https://patentimages.storage.googleapis.com/d0/4d/69/2960cd9f20dc88/US20100286171A1.pdfSearch in Google Scholar

7Jawed H, Ali Shah SU, Jamall S, Simjee SU. N-(2-hydroxy phenyl) acetamide inhibits inflammation-related cytokines and ROS inadjuvant-induced arthritic (AIA) rats. Int Immunopharmacol 2010;10:900–5. doi: 10.1016/j. intimp.2010.04.028Jawed H Ali Shah SU Jamall S Simjee SU N-(2-hydroxy phenyl) acetamide inhibits inflammation-related cytokines and ROS inadjuvant-induced arthritic (AIA) rats Int Immunopharmacol 201010900 5 10.1016/j.intimp.2010.04.02820452462Open DOISearch in Google Scholar

8Kaldrikyan MA, Grigoryan LA, Melik-Ogandzhanyan RG, Arsenyan FG. Synthesis and antitumor activity of some benzofuryl-substituted 1,2,4-triazoles. Pharm Chem J 2009;43:242–4. doi: 10.1007/s11094-009-0287-yKaldrikyan MA Grigoryan LA Melik-Ogandzhanyan RG Arsenyan FG Synthesis and antitumor activity of some benzofuryl-substituted 1,2,4-triazoles Pharm Chem J 200943242 4 10.1007/s11094-009-0287-yOpen DOISearch in Google Scholar

9Hirashima A, Yoshii Y, Eto M. Synthesis and biological activity of 2-aminothiazolines and 2-mercaptothiazolines as octopaminergic agonists. Agric Biol Chem 1991;55:2537–45. doi: 10.1080/00021369.1991.10871030Hirashima A Yoshii Y Eto M Synthesis and biological activity of 2-aminothiazolines and 2-mercaptothiazolines as octopaminergic agonists Agric Biol Chem 1991552537 45 10.1080/00021369.1991.10871030Open DOISearch in Google Scholar

10Okamoto H, Kato S, Kobutani T, Ogasawara M, Konnai M, Takematsu T. Herbicidally active N-(1-arylethenyl)-2-chloroacetamides bearing an alkyloxyalkyl moiety. Agric B i o l Chem 1 9 9 1 ; 5 5 : 2 7 3 7 – 4 3 . do i : 10.1080/00021369.1991.10871035Okamoto H Kato S Kobutani T Ogasawara M Konnai M Takematsu T Herbicidally active N-(1-arylethenyl)-2-chloroacetamides bearing an alkyloxyalkyl moiety Agric Biol Chem 1991 55 2737 43 10.1080/00021369.1991.10871035Open DOISearch in Google Scholar

11Antypenko OM, Antypenko LM, Kovalenko SI, Katsev AM, Achkasova OM. Potential of N-aryl(benzyl,heteryl)-2-(tetrazolo[1,5-c]quinazolin-5-ylthio)acetamides as anticancer and antimicrobial agents. Arab J Chem 2016;9:792–805. doi: 10.1016/j.arabjc.2014.09.009Antypenko OM Antypenko LM Kovalenko SI Katsev AM Achkasova OM Potential of N-aryl(benzyl,heteryl)-2-(tetrazolo[1,5-c]quinazolin-5-ylthio)acetamides as anticancer and antimicrobial agents Arab J Chem 20169792 805 10.1016/j.arabjc.2014.09.009Open DOISearch in Google Scholar

12Katke SA, Amrutkar SV, Bhor RJ, Khairnar MV. Synthesis of biologically active 2-Chloro-N-alkyl/aryl acetamide derivatives. Int J Pharma Sci Res 2011;2:148–56.Katke SA Amrutkar SV Bhor RJ Khairnar MV Synthesis of biologically active 2-Chloro-N-alkyl/aryl acetamide derivatives Int J Pharma Sci Res 20112148 56Search in Google Scholar

13Sharshira EM, Hamada NMM. Synthesis, characterization and antimicrobial activities of some thiazole derivatives. Am J Org Chem 2012;2:69–73. doi: 10.5923/j.ajoc.20120203.06Sharshira EM Hamada NMM Synthesis, characterization and antimicrobial activities of some thiazole derivatives Am J Org Chem 2012269 73 10.5923/j.ajoc.20120203.06Open DOISearch in Google Scholar

14Bilyi AK, Antypenko LM, Ivchuk VV, Kamyshnyi OM, Polishchuk NM, Kovalenko SI. 2-heteroaryl-[1,2,4] triazolo[1,5-c]quinazoline-5(6 H)-thiones and their S-substituted derivatives: synthesis, spectroscopic data, and biological activity. Chempluschem 2015;80:980–9. doi: 10.1002/cplu.201500051Bilyi AK Antypenko LM Ivchuk VV Kamyshnyi OM Polishchuk NM Kovalenko SI 2-heteroaryl-[1,2,4] triazolo[1,5-c]quinazoline-5(6 H)-thiones and their S-substituted derivatives: synthesis, spectroscopic data, and biological activity Chempluschem 201580980 9 10.1002/cplu.20150005131973251Open DOISearch in Google Scholar

15Goyal A, Tiwari M, Chaturvedi S. Synthesis and biological activities of glycolamide esters of cinmetacin. Asian J Chem 2005;17:631–3.Goyal A Tiwari M Chaturvedi S Synthesis and biological activities of glycolamide esters of cinmetacin Asian J Chem 200517631 3Search in Google Scholar

16Khan MSY, Khan RM. Synthesis and biological evaluation of glycolamide esters as potential prodrugs of some non-steroidal anti-inflammatory drugs. Indian J Chem B 2002;41:2172–5.Khan MSY Khan RM Synthesis and biological evaluation of glycolamide esters as potential prodrugs of some non-steroidal anti-inflammatory drugs Indian J Chem B 2002412172 5Search in Google Scholar

17Liang HY, Zhang DQ, Yue Y, Shi Z, Zhao SY. Synthesis and biological activity of some 1,3-dihydro-2H-3-benzazepin-2-ones with a piperazine moiety as bradycardic agents. Arch Pharm (Weinheim) 2010;343:114–9. doi: 10.1002/ ardp.200900169Liang HY Zhang DQ Yue Y Shi Z Zhao SY Synthesis and biological activity of some 1,3-dihydro-2H-3-benzazepin-2-ones with a piperazine moiety as bradycardic agents Arch Pharm (Weinheim) 2010343114 9 10.1002/ardp.20090016920108265Open DOISearch in Google Scholar

18Zhao G, Yang H. The synthesis and biological activity of N-arylaminocarbonylmethylene-1,2-benzothiazine 1,1-dioxides. Chinese Chem Lett 1996;7:1087–8.Zhao G Yang H The synthesis and biological activity of N-arylaminocarbonylmethylene-1,2-benzothiazine 1,1-dioxides Chinese Chem Lett 199671087 8Search in Google Scholar

19Matijević BM, Vaštag ĐĐ, Apostolova SLj, Milčić MK, Marinković AD, Petrović SD N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study. Arab J Chem 2019;12:3367–79. doi: 10.1016/j.arabjc.2015.09.008Matijević BM Vaštag ĐĐ Apostolova SLj Milčić MK Marinković AD Petrović SD N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study Arab J Chem 2019123367 79 10.1016/j.arabjc.2015.09.008Open DOISearch in Google Scholar

20Dhanda SK, Singla D, Mondal AK, Raghava GPS. DrugMint: A webserver for predicting and designing of drug-like molecules. Biol Direct 2013;8:28. doi: 10.1186/1745-61508-28Dhanda SK Singla D Mondal AK Raghava GPS DrugMint: A webserver for predicting and designing of drug-like molecules Biol Direct 2013828 10.1186/1745-61508-28Open DOISearch in Google Scholar

21Veber DF, Johnson SR, Cheng H-Y, Smith BR, Ward KW, Kopple KD. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 2002;45:2615– 23. doi: 10.1021/jm020017nVeber DF Johnson SR Cheng H-Y Smith BR Ward KW Kopple KD Molecular properties that influence the oral bioavailability of drug candidates J Med Chem 200245 2615 23 10.1021/jm020017n12036371Open DOISearch in Google Scholar

22Egan WJ, Merz KM Jr, Baldwin JJ. Prediction of drug absorption using multivariate statistics. J Med Chem 2000;43:3867–77. doi: 10.1021/jm000292eEgan WJ Merz KMJr Baldwin JJ Prediction of drug absorption using multivariate statistics J Med Chem 2000433867 77 10.1021/jm000292e11052792Open DOISearch in Google Scholar

23Calculation of Molecular Properties and Bioactivity Score [displayed 22 February 2021]. Available at https://www.molinspiration.com/cgi-bin/propertiesCalculation of Molecular Properties and Bioactivity Score [displayed 22 February 2021] Available at https://www.molinspiration.com/cgi-bin/propertiesSearch in Google Scholar

24Swiss Institute of Bioinformatics. SwisADME [displayed 22 February 2021]. Available at http://www.swissadme.ch/Swiss Institute of Bioinformatics. SwisADME [displayed 22 February 2021] Available at http://www.swissadme.ch/Search in Google Scholar

25PreADMET [displayed 22 February 2021]. Available at https://preadmet.bmdrc.krPreADMET [displayed 22 February 2021] Available at https://preadmet.bmdrc.krSearch in Google Scholar

26LabWorm. pkCSM [displayed 22 February 2021]. Available at: https://labworm.com/tool/pkcsmLabWorm. pkCSM [displayed 22 February 2021] Available at https://labworm.com/tool/pkcsmSearch in Google Scholar

27Sarker SD, Nahar L, Kumarasamy Y. Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth and its application in the in vitro antibacterial screening of phytochemicals. Methods 2007;42:321–4. doi: 10.1016/j.ymeth.2007.01.006Sarker SD Nahar L Kumarasamy Y Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth and its application in the in vitro antibacterial screening of phytochemicals Methods 200742321 4 10.1016/j.ymeth.2007.01.006189592217560319Open DOISearch in Google Scholar

28Ugwu DI, Okoro UC, Mishra NK. Synthesis, characterization and in vitro antitrypanosomal activities of new carboxamides bearing quinoline moiety. PLoS One 2018;13(1):e0191234. doi: 10.1371/journal.pone.0191234Ugwu DI Okoro UC Mishra NK Synthesis, characterization and in vitro antitrypanosomal activities of new carboxamides bearing quinoline moiety PLoS One 2018131e0191234 10.1371/journal.pone.0191234576448129324817Open DOISearch in Google Scholar

29Loureiro DPR, Soares JX, Costa JC, Magakhaes AF, Azevedo CMG, Pinto MMM, Alfonso CMM. Structures, activities and drug-likeness of anti-infective xanthone derivatives isolated from the marine environment: a review. Molecules 2019;24:243. doi: 10.3390/molecules24020243Loureiro DPR Soares JX Costa JC Magakhaes AF Azevedo CMG Pinto MMM Alfonso CMM Structures, activities and drug-likeness of anti-infective xanthone derivatives isolated from the marine environment: a review Molecules 201924243 10.3390/molecules24020243635955130634698Open DOISearch in Google Scholar

30Lazić A, Mandić Ž, Valentić N, Ušćumlić G, Trišović N. Dizajn, sinteza novih spirohidantoina izvedenih iz beta-tetralona i evaluacija njihovih farmakokinetički relevanthih svojstava [New spirohydantoins derived from β-tetralone: design, synthesis and evaluation of their pharmacokinetically relevant propertie, in Serbian]. Hem Ind 2019;73:79–92. doi: 10.2298/HEMIND181203007LLazić A Mandić Ž Valentić N Ušćumlić G Trišović N Dizajn, sinteza novih spirohidantoina izvedenih iz beta-tetralona i evaluacija njihovih farmakokinetički relevanthih svojstava [New spirohydantoins derived from β-tetralone: design, synthesis and evaluation of their pharmacokinetically relevant propertie, in Serbian] Hem Ind 20197379 92 10.2298/HEMIND181203007LOpen DOISearch in Google Scholar

31Garcia-Sosa AT, Maran U, Hetenyi C. Molecular property filters describing pharmacokinetics and drug binding. Curr M e d Chem 2 0 1 2 ; 1 9 : 1 6 4 6 – 6 2 . do i : 10.2174/092986712799945021Garcia-Sosa AT Maran U Hetenyi C Molecular property filters describing pharmacokinetics and drug binding Curr Med Chem 2012 19 1646 62 10.2174/09298671279994502122376034Open DOISearch in Google Scholar

32Singh SK, Gaur R, Kumar A, Fatima R, Mishra L, Srikrishna S. The flavonoid derivative 2-(4′ Benzyloxyphenyl)-3-hydroxy-chromen-4-one protects against Aβ42-induced neurodegeneration in transgenic drosophila: insights from in silico and in vivo studies. Neurotox Res 2014;26:331–50. doi: 10.1007/s12640-014-9466-zSingh SK Gaur R Kumar A Fatima R Mishra L Srikrishna S The flavonoid derivative 2-(4′ Benzyloxyphenyl)-3-hydroxy-chromen-4-one protects against Aβ42-induced neurodegeneration in transgenic drosophila: insights from in silico and in vivo studies Neurotox Res 201426331 50 10.1007/s12640-014-9466-z24706035Open DOISearch in Google Scholar

33Sharma D, Kumar S, Narasimhan B, Ramasamy K, Lim S M, Ali Shah S, Mani V. Synthesis, molecular modelling and biological significance of N(4-(4‑bromophenyl) derivatives as prospective antimicrobial and antiproliferative agents BMC Chem 2019;13:46–60. doi: 10.1186/s13065-019-0564-0Sharma D Kumar S Narasimhan B Ramasamy K Lim S M Ali Shah S, Mani V Synthesis, molecular modelling and biological significance of N(4-(4‑bromophenyl) derivatives as prospective antimicrobial and antiproliferative agents BMC Chem 20191346 60 10.1186/s13065-019-0564-0666196731384794Open DOISearch in Google Scholar

34Singh DCP, Hashim SR, Singhal RG. Synthesis and antimicrobial activity of some new thioether derivatives of q u in o x a l in e . E- J Chem 2 0 11 ; 8 : 6 3 5 – 4 2 . do i : 10.1155/2011/482831Singh DCP Hashim SR Singhal RG Synthesis and antimicrobial activity of some new thioether derivatives of quinoxaline E- J Chem 2011 8 635 42 10.1155/2011/482831Open DOISearch in Google Scholar

35Hamm PC, Speziale AJ. Relation of herbicidal activity to the amide moiety of N-substituted alpha-chloroacetamides. J Agric Food Chem 1956;4:518–22. doi: 10.1021/jf60064a001Hamm PC Speziale AJ Relation of herbicidal activity to the amide moiety of N-substituted alpha-chloroacetamides J Agric Food Chem 19564518 22 10.1021/jf60064a001Open DOISearch in Google Scholar

36Constantinescu T, Lungu CN, Lung I. Lipophilicity as a central component of drug-like properties of chalchones and flavonoid derivatives. Molecules 2019;24:1505–16. doi: 10.3390/molecules24081505Constantinescu T Lungu CN Lung I Lipophilicity as a central component of drug-like properties of chalchones and flavonoid derivatives Molecules 2019241505 16 10.3390/molecules24081505651505430999606Open DOISearch in Google Scholar

37Jablonkai I. Alkylating reactivity and herbicidal activity of chloroacetamides. Pest Manag Sci 2003;59:443–50. doi: 10.1002/ps.634Jablonkai I Alkylating reactivity and herbicidal activity of chloroacetamides Pest Manag Sci 200359443 50 10.1002/ps.63412701706Open DOISearch in Google Scholar