14736-50-6Relevant articles and documents
Design, Synthesis, and Structural Analysis of Cladosporin-Based Inhibitors of Malaria Parasites
Babbar, Palak,Das, Pronay,Manickam, Yogavel,Mankad, Yash,Yadav, Swati,Parvez, Suhel,Sharma, Amit,Reddy, D. Srinivasa
, p. 1777 - 1794 (2021/05/10)
Here we have described a systematic structure activity relationship (SAR) of a set of compounds inspired from cladosporin, a tool compound that targets parasite (Plasmodium falciparum) lysyl tRNA synthetase (KRS). Four sets of analogues, synthesized based on point changes in the chemical scaffold of cladosporin and other logical modifications and hybridizations, were assessed using high throughput enzymatic and parasitic assays along with in vitro pharmacokinetics. Co-crystallization of the most potent compound in our series (CL-2) with PfKRS revealed its structural basis of enzymatic binding and potency. Further, we report that CL-2 has performed better than cladosporin in terms of metabolic stability. It thus represents a new lead for further optimization toward the development of antimalarial drugs. Collectively, along with a lead compound, the series offers insights on how even the slightest chemical modification might play an important role in enhancing or decreasing the potency of a chemical scaffold.
Highly chemoselective esterification reactions and Boc/THP/TBDMS discriminating deprotections under samarium(III) catalysis
Gopinath, Pushparathinam,Nilaya, Surapaneni,Muraleedharan, Kannoth Manheri
supporting information; experimental part, p. 1932 - 1935 (2011/06/21)
The usefulness of SmCl3 as an excellent catalyst for chemoselective esterifications and selective removal of acid sensitive protecting groups such as Boc, THP, and TBDMS in the presence of one another is demonstrated through suitable examples.
The chemistry of homophthalic acid: a new synthetic strategy for construction of substituted isocoumarin and indole skeletons
?zcan, Sevil,Balci, Metin
, p. 5531 - 5540 (2008/09/21)
Homophthalic acid was reacted with thionylchloride/DMF and chloroethylformate/NEt3 in the presence and absence of NaN3. In all cases completely different isocoumarin derivatives were obtained. These unusual isocoumarin derivatives were isolated and characterized and their formation mechanisms are discussed. The homophthalic acid monomethyl ester was converted into the corresponding isocyanate. Reaction of the isocyanate with different amines produced the urea derivatives. Base-supported condensation reactions of these products gave first an indolinone derivative, which underwent further intermolecular condensation to give substituted indole derivatives. However, when the condensation reaction was carried out in the presence of acetic anhydride, the intermolecular reactions were suppressed. This methodology opens up a new way of synthesizing of various five-membered ring substituted indole derivatives.