Synthesis and biological evaluation of some coumarin hybrids as selective carbonic anhydrase IX and XII inhibitors was written by Thacker, Pavitra S.;Sridhar Goud, Nerella;Argulwar, Omkar S.;Soman, Jyothsna;Angeli, Andrea;Alvala, Mallika;Arifuddin, Mohammed;Supuran, Claudiu T.. And the article was included in Bioorganic Chemistry in 2020.Synthetic Route of C6H9ClO3 The following contents are mentioned in the article:
Two series, coumarin-linked to thiazolidinone via a pyrazole linker I [R = H, 3-Me, 4-Cl, etc.] and coumarin-linked 1,2,3-triazoles II [R1 = H, 4-MeO, 3-Cl, etc.] were synthesized and were subjected for evaluation against the four physiol. and pharmacol. relevant hCA isoforms, hCA I, II, IX and XII. The results indicated selective inhibition of tumor-associated isoforms hCA IX and XII over the off-target isoforms, hCA I and II. The compounds I exhibited better hCA IX inhibition compared to hCA XII, with compounds I [R = 3-Me, 3-F3C, 4-Me, 4-MeO] exhibited notable Ki values of less than 100 nM. Among all the compounds, compound I [R = 3-Me] showed the best inhibition with a Ki value of 61.5 nM. Among the compounds of II, compounds II [R1 = H, 4-O2N, 2,5-di-Cl, 4-CN, 4-Me, 3-Cl] exhibited notable hCA IX inhibition. Compound II [R1 = 4-CN] showed the best inhibition with a Ki value of 32.7 nM. In the case of hCA XII, compound II [R1 = 4-MeO] showed the best inhibition with a Ki value of 84.2 nM. Hence, compound I [R = 3-Me] and II [R1 = 4-CN] could be taken as lead compounds for the further development of selective and potent hCA IX inhibitors, whereas the compound II [R1 = 4-MeO] can be explored further for the design of selective and potent hCA XII inhibitors. This study involved multiple reactions and reactants, such as Ethyl 4-chloro-3-oxobutanoate (cas: 638-07-3Synthetic Route of C6H9ClO3).
Ethyl 4-chloro-3-oxobutanoate (cas: 638-07-3) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications.While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.Synthetic Route of C6H9ClO3
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics