759-65-9Relevant academic research and scientific papers
CONDENSED AZAHETEROARYL COMPOUNDS HAVING ANTIBACTERIAL ACTIVITY AGAINST TUBERCULOSIS BACTERIA
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Page/Page column 17, (2020/01/08)
Present invention relates to novel compound of general formula (I), their enantiomers, their diastereomers, their pharmaceutically accepted salts, or pro-drugs thereof, which are useful for the treatment of bacterial infection. The compounds of general formula (I) exhibit DprE1 enzyme inhibitory activity.
AZAINDOLE COMPOUNDS, SYNTHESIS THEREOF, AND METHODS OF USING THE SAME
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Paragraph 0168; 0237; 0238, (2015/02/18)
The invention provides compounds of formula (I) and methods of treating a Mycobacterium infection or tuberculosis, or inhibiting DprE1 with the same.
Azaindoles: Noncovalent DprE1 inhibitors from scaffold morphing efforts, kill Mycobacterium tuberculosis and are efficacious in vivo
Shirude, Pravin S.,Shandil, Radha,Sadler, Claire,Naik, Maruti,Hosagrahara, Vinayak,Hameed, Shahul,Shinde, Vikas,Bathula, Chandramohan,Humnabadkar, Vaishali,Kumar, Naveen,Reddy, Jitendar,Panduga, Vijender,Sharma, Sreevalli,Ambady, Anisha,Hegde, Naina,Whiteaker, James,McLaughlin, Robert E.,Gardner, Humphrey,Madhavapeddi, Prashanti,Ramachandran, Vasanthi,Kaur, Parvinder,Narayan, Ashwini,Guptha, Supreeth,Awasthy, Disha,Narayan, Chandan,Mahadevaswamy, Jyothi,Vishwas,Ahuja, Vijaykamal,Srivastava, Abhishek,Prabhakar, Kr,Bharath, Sowmya,Kale, Ramesh,Ramaiah, Manjunatha,Choudhury, Nilanjana Roy,Sambandamurthy, Vasan K.,Solapure, Suresh,Iyer, Pravin S.,Narayanan, Shridhar,Chatterji, Monalisa
supporting information, p. 9701 - 9708 (2014/01/06)
We report 1,4-azaindoles as a new inhibitor class that kills Mycobacterium tuberculosis in vitro and demonstrates efficacy in mouse tuberculosis models. The series emerged from scaffold morphing efforts and was demonstrated to noncovalently inhibit decaprenylphosphoryl-β-D-ribose2′-epimerase (DprE1). With "drug-like" properties and no expectation of pre-existing resistance in the clinic, this chemical class has the potential to be developed as a therapy for drug-sensitive and drug-resistant tuberculosis.
Evidence for Ketene Intermediates in the Reactions of 2-Oxobutanedioic Acid Diesters with Alcohols and Water
Emerson, David W.,Titus, Richard L.,Gonzalez, Rowena M.
, p. 3572 - 3576 (2007/10/02)
The reactions of diethyl ester (1a) and dimethyl ester (1b) of 3-methyl-2-oxobutanedioic acid with excess ethanol, methanol, or water in a sealed tube at approximately 125 deg C were studied.With methanol, 1a yielded mainly 3-methyl-2-oxobutanedioic acid 1-ethyl 4-methyl diester, 2a; with ethanol, 1b yielded mainly the 4-ethyl 1-methyl diester, 2b, while reaction of 1a with water yielded carbon dioxide, 2-oxobutanoic acid ethyl ester, 6, and 2-methyl-3-oxopropanoic acid ethyl ester, 7.These results suggested that the ketene intermediates 3-methyl-2,4-dioxo-3-butenoic acid ethyl or methyl ester, 4a and 4b, respectively, are implicated.The similarity of these reactions to those exhibited by ethyl acetoacetate, such as alkoxy group exchange, and formation of dehydroacetic acid, now thought to proceed by way of acetyl ketene, was demonstrated.
Synthesis of the (Z) and (E) Isomers of 1,2-Diaryl-3-methyl-4,5-dioxo-3-pyrrolidinecarboxylic Acid Esters. Structural Assignment by NMR and Mass Spectroscopy
Titus, Richard L.,Emerson, David W.,Gonzales, Rowena M.
, p. 1857 - 1860 (2007/10/02)
Reaction of N-benzylideneaniline, 1a, with 3-methyl-2-oxobutanedioic acid diethyl ester, 2a, produced isomeric 3-methyl-4,5-dioxo-1,2-diphenyl-3-pyrrolidinecarboxylic acid ethyl esters, 3a and 3b.The higher melting isomer, 3a, was shown to have (Z) configuration by nmr spectroscopy.The (Z) and (E) isomers of 3-methyl-4,5-dioxo-1,2-diphenyl-3-pyrrolidinecarboxylic acid methyl esters, 3c and 3d, were prepared from 1a and 3-methyl-2-oxobutanedioic acid dimethyl ester, 2b.The higher melting isomer, 3c, was shown to have the (Z) configuration.Similarly, N-benzylidene-p-toluidine, 1b, reacted with 2a to form (Z) and (E) isomers of 3-methyl-4,5-dioxo-1-(4-methylphenyl)-2-phenyl-3-pyrrolidinecarboxylic acid ethyl esters, 3e and 3f.Assignment o the 13C carbonyl carbon nmr chemical shift was made by preparing 2-methyl-3-oxobutanedioic-1-13C acid diethyl ester, 4, and from it the corresponding (Z) and (E) isomers of 3-methyl-4,5-dioxo-1,2-diphenyl-3-pyrrolidinecarboxylic 13C acid ester, 5a and 5b.The mass spectra of the (Z) isomers exhibit prominent ions corresponding to the masses of the Schiff bases used to make them, and ions corresponding to the loss of Ar-NCOCO from the parent ion.The (E) isomers 3b, 3d and 5b exhibit a prominent ion of mass 264; 3f gives mass 278, corresponding to the loss of the carboalkoxy group.
Some Sulfur-containing Quinoxalines (1)
Campaigne, E.,McLaughlin, Astley R.
, p. 623 - 628 (2007/10/02)
A series of quinoxalines having oxygen, chlorine or sulfur substituted at the 2-position and long-chain alkyl, alkylthio, arylthio, alkylthioalkyl or arylthioalkyl groups at the 3-position have been synthesized.
