193139-67-2

Basic information

• Product Name: 1(2H)-Quinolinecarboxylic acid, 2-ethynyl-4-(hydroxymethyl)-, 4-fluorophenyl ester
• CAS NO: 193139-67-2
• Molecular Formula: C19H14FNO3
• Molecular Weight: 323.323
• Mol File: 193139-67-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1(2H)-Quinolinecarboxylic acid, 2-ethynyl-4-(hydroxymethyl)-, 4-fluorophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1(2H)-Quinolinecarboxylic acid, 2-ethynyl-4-(hydroxymethyl)-, 4-fluorophenyl ester(193139-67-2)
• EPA Substance Registry System: 1(2H)-Quinolinecarboxylic acid, 2-ethynyl-4-(hydroxymethyl)-, 4-fluorophenyl ester(193139-67-2)

Safety Data

• Hazardous Substances Data: 193139-67-2(Hazardous Substances Data)

Upstream product

• 156741-27-4 4-(((tert-butyldimethylsilyl)oxy)methyl)quinoline 
• 38377-38-7 4-fluorophenyl chloroformate 
• 193139-58-1 4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-ethynyl-2H-quinoline-1-carboxylic acid 4-fluoro-phenyl ester 

Relevant articles and documents

Activity relationships of cyclic enediynes related to dynemicin A-I. Synthesis and antitumor activity of 9-acetoxy enediynes equipped with aryl carbamate moieties

A series of the 9-acetoxy enediyne compounds, 6a-k which were simplified from natural dynemicin A, and designed to be equipped with various aryl carbamate moieties, was synthesized and evaluated for DNA-cleaving ability, in vitro cytotoxicity, and in vivo antitumor activity. As a result of this study of the structure-activity relationships (SAR) with regard to the R1 substituent, both compounds 6a and 6f with the phenyl carbamate and 4-chlorophenyl carbamate moiety, respectively, were found to exhibit significant activity (T/C > 200%) against murine P388 leukemia in mice, in spite of having IC50 values in the micromolar range. In particular, compound 6f showed the most potent activity with a maximum T/C of 256% at a daily dosage of 4.0 mg/kg for four days. Furthermore, both compounds 6a and 6f were effective against Meth A sarcoma in mice and inhibited 71 and 77% of the tumor growth at 2.0 and 3.0 mg/kg dosages, respectively. In contrast to 6f, compound 6i possessing the 2-nitrophenyl carbamate moiety showed only a slight in vivo activity, while it had about one order of magnitude higher in vitro cytotoxicity than 6f. For the stereochemistry-activity relationships at the C9 position, the (9R(@,))-isomers of 6c, 6g, and 6j were found to show higher in vitro and in vivo potencies than the corresponding 9S(@,))-isomers.