02441nas a2200265   4500008004100000022001400041245017700055210006900232260000900301300001600310490000600326520144600332653002401778653002201802653001701824653003101841653003501872100002401907700002201931700002401953700002001977700002201997700002502019856013102044       2019                        eng d  a2365-654900aCyanuric-chloride-mediated synthesis of 2-Aryl-3-tert-butoxycarbonyl-thiazolidine-4-carboxylic acid anilides: mechanistic, X-ray crystal structures and cytotoxicity studies0 aCyanuricchloridemediated synthesis of 2Aryl3tertbutoxycarbonylth  cNOV   a12534-125460 v43 a<p>The `2R,4R'-2-aryl thiazolidine-4-carboxylic acid anilides (ATCAAs) were synthesized using cyanuric chloride (CC) as a clean and substoichiometric acid-amine coupling agent under optimized reaction conditions. The diesterphenol intermediate based mechanism is proposed and supported by spectral characterization of the intermediate. The single crystal X-ray structures of acid substrate (2R,4R)-3-(tert-butoxycarbonyl)-2-(2-methoxyphenyl)thiazolidine-4-carbox ylic acid (3 a) and anilides (R)-tert-butyl 4-(2-fluorophenylcarbamoyl)thiazolidine-3-carboxylate (4 b), (2R,4R)-tert-butyl 2-(2,6-dichlorophenyl)-4-(m-tolylcarbamoyl)thiazolidine-3-carboxylate (6 b) confirmed the formation of chiral anilides. The synthesized library of anilides [(R)-tert-butyl 4-Aryl thiazolidine-3-carboxylate and (2R,4R)-tert-butyl 2-Aryl-4-Aryl thiazolidine-3-carboxylate] 4 a-6 f was screened for their in vitro anti cancer, neuronal and neuroprotective studies. The anilides 4 b, 4 g, 5 d, 5 h, 6 c and 6 f (where the aryl=2-fluorophenylcarbamoyl, 4-chlorophenylcarbamoyl, 2-methoxyphenyl, 2,5-dichlorophenylcarbamoyl, 2,6-dichlorophenyl, 4-chlorophenylcarbamoyl respectively)were found to be less cytotoxic towards N2 A, SHSY-5Y neuronal cell lines in their differentiated and undifferentiated forms, and also exhibited dose dependant anti-inflammatory properties for a possible identification towards neurodegenerative and inflammatory disorders.</p>
10aAcid-amine coupling10aCyanuric chloride10aCytotoxicity10aMechanistic investigations10aSingle crystal x-ray structure1 aJagtap, Rohidas, M.1 aShaikh, Samir, R.1 aGonnade, Rajesh, G.1 aRaheem, Shabnam1 aRizvi, Masood, A.1 aPardeshi, Satish, K.  uhttps://library.ncl.res.in/content/cyanuric-chloride-mediated-synthesis-2-aryl-3-tert-butoxycarbonyl-thiazolidine-4-carboxylic