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Research Articles

Serendipitous discovery of a regioselective synthesis of novel benzoyloxy substituted phenyl/benzyl-sulfanyl/selenylbisesters, 3-benzoyloxy-3-(phenylsulfanyl)-β-lactams and their antimicrobial evaluation

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Pages 712-732 | Received 02 Mar 2023, Accepted 19 Jun 2023, Published online: 11 Jul 2023

References

  • Silva MM, Lidon FC. Food preservatives – an overview on applications and side effects. Emir J Food Agric. 2016;28:366–373. DOI:10.9755/ejfa.2016-04-351
  • Solovev VA, Sokolnikov AS. Aerosol-forming composition for fire suppression. European Patent EP. 2021 Aug 04;3:858,444 A1.
  • Xu GG, Pagare PP, Ghatge MS, et al. Design, synthesis, and biological evaluation of ester and ether derivatives of antisickling agent 5-HMF for the treatment of sickle cell disease. Mol Pharm. 2017;14:3499–3511. DOI:10.1021/acs.molpharmaceut.7b00553
  • Zhou NE, Guo D, Thomas G, et al. 3-Acylamino-azetidin-2-one as a novel class of cysteine proteases inhibitors. Bioorg Med Chem Lett. 2003;13:139–141. DOI:10.1016/S0960-894X(02)00831-4
  • Adlington RM, Baldwin JE, Chen B, et al. Design and synthesis of novel monocyclic β-lactam inhibitors of prostate specific antigen. Bioorg Med Chem Lett. 1997;7:1689–1694. DOI:10.1016/S0960-894X(97)00285-0
  • Smit FJ, Biljon RA, van Birkholtz L, et al. Synthesis and in vitro biological evaluation of dihydroartemisinyl-chalcone esters. Eur J Med Chem. 2015;90:33–44. DOI:10.1016/j.ejmech.2014.11.016
  • Husein AI, Jondi WJ, Zatar NA, et al. Synthesis and biological evaluation of novel mono acid esters derived from the constituents of Urtica pilulifera. Iran J Pharm Res. 2014;13:1173–1181. .DOI:10.22037/ijpr.2014.1571
  • Hermange P, Portalier F, Thomassigny C, et al. Practical one-pot sequence for the asymmetric synthesis of 1,2 diols from primary alcohols. Tetrahedron Lett. 2013;54:1052–1055. DOI:10.1016/j.tetlet.2012.11.137
  • Demoulin N, Lifchits O, List B. Organocatalytic asymmetric α-benzoyloxylation of α-branched aldehydes and enals: a useful approach to oxygenated quaternary stereocenters. Tetrahedron. 2012;68:7568–7574. DOI:10.1016/j.tet.2012.06.043
  • Jadhav MS, Righi P, Marcantoni E, et al. Enantioselective α-benzoyloxylation of ketones promoted by primary amine catalyst. J Org Chem. 2012;77:2667–2674. DOI:10.1021/jo2024976
  • Piras E, Secci F, Caboni P, et al. α-Benzoyloxylation of β-keto sulfides at ambient temperature. RSC Adv. 2017;7:49215–49219. DOI:10.1039/C7RA10888E
  • Hirose T, Morita N, Asakura M, et al. Formation of 3-(m-chlorobenzoyloxy)-2-(phenylseleno)propan-1-ol and 2-(m-chlorobenzoyloxy)-3-(phenylseleno)propan-1-ol from a reaction of allyl phenyl selenide with m-chloroperoxybenzoic acid. Tetrahedron Lett. 1998;39:8877–8880. DOI:10.1016/S0040-4039(98)02020-6
  • Junior HP, Oliveira MFB, Gambero S, et al. Randomized clinical trial of famciclovir or Acyclovir for the treatment of herpes zoster in adults. Int J Infect Dis. 2018;72:11–15. DOI:10.1016/j.ijid.2018.04.4324
  • Sklavounos C, Crawford TC. Bis-esters of methanediol with acetonides of ampicillin or amoxicillin and penicillanic acid 1,1-dioxide. UK Patent GB 2,095,249 A. 1982 Sep 29.
  • Jia Q, Du X, Wang C, et al. A one-pot synthesis of a self-included bisester-functionalized copillar [5] arene. Chin Chem Lett. 2019;30:721–724. DOI:10.1016/j.cclet.2018.12.015
  • Diwedi R, Alexander S, Chandrasekar MJN. Rapid and efficient synthesis of microwave assisted some bis-1,2,4-triazole derivatives and their antioxidant and anti-inflammatory evaluation. Res J Pharm Biol Chem Sci. 2011;2:194–204.
  • Bandgar BP, Sarangdhar RJ, Fruthous K, et al. Synthesis and biological evaluation of ester prodrugs of benzafibrate as orally active hypolipidemic agents. Eur J Med Chem. 2012;57:217–224. DOI:10.1016/j.ejmech.2012.08.036
  • Huang LJ, Li CH, Lu ZM, et al. Total synthesis and biological evaluation of (1)- and (2)-butyl ester of rosmarinic acid. J Asian Nat Prod Res. 2006;8:561–566. DOI:10.1080/10286020500176229
  • Shibata N, Matsugi M, Kawano N, et al. Highly asymmetric Pummerer-type reaction induced by ethoxy vinyl esters. Tetrahedron Asymm. 1997;8:303–310. DOI:10.1016/S0957-4166(96)00510-1
  • Cainelli G, Angeloni C, Cervellati R, et al. New polyphenolic β-lactams with antioxidant activity. Chem Bio Divers. 2008;5:811–829. .DOI:10.1002/cbdv.200890077
  • Turos E, Coates C, Shim J, et al. N-Methylsulfanyl β-lactam antibacterials: effects of the C3/C4 ring substituents on anti-MRSA activity. Bioorg Med Chem. 2005;13:6289–6308. DOI:10.1016/j.bmc.2005.08.011
  • Gottstein WJ, Haynes UJ, McGregor DN. Synthesis and β-lactamase inhibitory properties of 2β-[(acy1oxy)methyl]-2-methylpenam-3α-carboxylic acid 1,1-dioxides. J Med Chem. 1985;28:518–522. DOI:10.1021/jm00382a025
  • Matsumura H, Yano T, Ueyama M, et al. Direct introduction of a benzoyloxy substituent at the ring junction of fused β-lactam rings. J Chem Soc Chem Commun. 1979: 485–486. DOI:10.1039/C39790000485
  • Easton CJ, Love SG, Wang P. Acyloxylation at the 4-position of azetidin-2-ones. J Chem Soc Perkin Trans. 1990;11:277–282. DOI:10.1039/p19900000277
  • Easton CJ, Love SG. Direct introduction of a benzoyloxy substituent at the C-4 position of β-lactams. Tetrahedron Lett. 1986;27:2315–2318. DOI:10.1016/S0040-4039(00)84518-9
  • Sunagawa M, Matsumura H, Inoue T. De-arylmethylation of N-mono- or N-diarylmethyl-beta-lactams; Novel azetizinones having anti-bacterial activity. European Patent EP. 1984 Aug 01;0023097 B1.
  • Sunagawa M, Matsumura H, Inoue T. Sumitomo chemical company, assignee. Preparation of β-lactam derivatives. United States patent US 4,536,334. 1985 Aug 20.
  • Narula D, Bari SS, Yadav P, et al. Synthesis of α-heterocycle anchored spirocyclic azetidin-2-ones in a minute by p-TSA catalyzed cyclocondensation of azetidin-2,3-diones with difunctionalized substrates. ChemistrySelect. 2021;6:3932–3940. DOI:10.1002/slct.202101104
  • Bhalla A, Madan S, Venugopalan P, et al. C-3 β-Lactam carbocation equivalents: versatile synthons for C-3 substituted β-lactams. Tetrahedron. 2006;62:5054–5063. DOI:10.1016/j.tet.2006.03.050
  • Bhalla A, Venugopalan P, Bari SS. Facile stereoselective synthesis of cis- and trans-3-alkoxyazetidin-2-ones. Tetrahedron. 2006;62:8291–8302. DOI:10.1016/j.tet.2006.06.062
  • Bari SS, Arora R, Bhalla A. Facile synthesis of (Z)- and (E)-3-allylidene-β-lactams via thermal β-elimination of trans-3-allyl-3-sulfinyl-β-lactams. Tetrahedron Lett. 2010;51:1719–1722. DOI:10.1016/j.tetlet.2010.01.085
  • Bhalla A, Modi G, Bari SS, et al. Stereoselective synthesis of novel C-3 functionalized 3-sulfonyl-β-lactams: promising biologically active heterocyclic scaffolds. Tetrahedron Lett. 2017;58:1160–1165. DOI:10.1016/j.tetlet.2017.02.011
  • He Y, Li N, Chen J, et al. Fe-mediated S-S bond cleavage and its application in the synthesis of α-arylsulfanyl carbonyl compounds. Synth Commun. 2015;45:1817–1822. DOI:10.1080/00397911.2015.1050037
  • Bhalla A, Sharma S, Bhasin KK, et al. Convenient preparation of benzylseleno- and phenylseleno alkanoic acids: Reagents for synthesis of organoselenium compounds. Synth Commun. 2007;37:783–793. DOI:10.1080/00397910601133540
  • Flowers GC, Leffler JE. Decomposition of bis(p-methoxybenzoyl) peroxide and the carboxy inversion product on silica. J Org Chem. 1985;50:4406–4408. DOI:10.1021/jo00222a048
  • Peng K, Zhi-Bing D. Recent advances in cross-dehydrogenative couplings (CDC) of C-H bond in aqueous media. Adv Synth Catal. 2021;363:1185–1201. DOI:10.1002/adsc.202001358
  • Salman M, Zhu ZQ, Huang ZZ. Dehydrogenative cross-coupling reaction between N–aryl α–amino acid esters and phenols or phenol derivative for synthesis of α–aryl α–amino acid esters. Org. Lett. 2016;18:1526–1529. DOI:10.1021/acs.orglett.6b00162
  • Xu Z, Yu X, Feng X, et al. Arylglycine-derivative synthesis via oxidative sp3 C-H functionalization of α-amino esters. Beilst J Org Chem. 2012;8:1564–1568. DOI:10.3762/bjoc.8.178
  • Kamal R, Kumar V, Bhardwaj V, et al. Synthesis, characterization and in vitro antimicrobial evaluation of some novel hydrazone derivatives bearing pyrimidinyl andpyrazolyl moieties as a promising heterocycles. Med Chem Res. 2015;24:2551–2560. DOI:10.1007/s00044-014-1313-5

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