13781-67-4Relevant articles and documents
Synthesis of two novel cysteine-functionalized thiophenes
Cagnoli, Rita,Lanzi, Massimiliano,Mucci, Adele,Parenti, Francesca,Schenetti, Luisa
, p. 267 - 271 (2005)
The synthetic approach to methyl N-(tert-butoxycarbonyl)-S-(3-thienyl)-L- cysteinate (1) and methyl N-(tert-butoxycarbonyl)-S-[2-(3-thienyl)ethyl]-L- cysteinate (2) through tosylate intermediates is reported and discussed. These compounds, which combine the properties of the cysteine side-chain with those of the thiophene ring represent both potential bioactive molecules and interesting synthons for the development of new materials.
Synthesis and evaluation of 4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran] analogues against both active and dormant Mycobacterium tuberculosis
Alluri, Kiran Kumar,Reshma, Rudraraju Srilakshmi,Suraparaju, Raghuram,Gottapu, Suryanarayana,Sriram, Dharmarajan
, p. 1462 - 1469 (2018)
Need for new drugs to fight against tuberculosis (TB) is increasing day by day. In the present work we have taken a spiro compound (GSK 2200150A) reported by GSK as a lead and we modified the structure of the lead to study the antitubercular activity. For structure activity profiling twenty-one molecules have been synthesized, characterized and evaluated for their antimycobacterial potency against both active and dormant TB. Compound 06, 1-((4-methoxyphenyl)sulfonyl)-4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran] was found to be the most potent compound (MIC: 8.23 μM) in active TB and was less effective than the lead but more potent than standard first line drug ethambutol. It was also found to be more efficacious than Isoniazid and Rifampicin and equipotent as Moxifloxacin against dormant Mycobacterium tuberculosis (MTB). Compound 06 also showed good inhibitory potential against over expressed latent MTB enzyme lysine ε-amino transferase with an IC50 of 1.04 ± 0.32 μM. This compound is a good candidate for drug development owing to potential against both active and dormant stages of MTB.
Synthesis of an ORL-1 Receptor Antagonist via a Radical Bromination and Deoxyfluorination to Afford a gem-Difluorospirocycle
Debaillie, Amy C.,Jones, Chauncey D.,Magnus, Nicholas A.,Mateos, Carlos,Torrado, Alicia,Wepsiec, James P.,Tokala, Ramachandar,Raje, Prasad
, p. 1568 - 1575 (2015/11/28)
The development of a synthesis of an ORL-1 receptor antagonist is described. The key process improvements in the synthetic sequence include a multikilogram bromination process and the development of a convergent coupling strategy. The process improvements resulted in the production of the active pharmaceutical ingredient (API) on a multikilogram scale.