Carbohydrate-based chiral organocatalysts

Tiwari, Vinod K.; Pellissier, Hélène

doi:10.1016/b978-0-323-91729-2.00021-5

Cited by 1 publication

(1 citation statement)

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“…Mycobacterium tuberculosis resides in macrophages, the primary defense system of the host, and it was envisioned to synthesize some potential glycohybrid compounds which can penetrate the macrophages. Carbohydrates as earlier discussed have the potential for structural diversity [18][19][20][21][22][23][24][25] and have some crucial roles in the diverse biological process, notably hostpathogen interactions [26], signal transduction [27], and also infammations [28,29]. Because of the abovementioned reasons, we have synthesized substituted glycosyl ureas and their derivatives to see the structure-activity relationship (SAR) against M. tuberculosis and, at the same time, possessed in vitro activity as it would lead to a good candidate for the successful development of a mechanism-based new class of antituberculosis drug candidates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antitubercular Evaluation of Diverse Glycosylated Ureas from D-Glucose

Tripathi,

Tiwari

2024

Journal of Chemistry

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N, N-disubstituted glycosylated ureas have been synthesized in good-to-excellent yields by 1,4-conjugate addition of amines to glycosylated olefinic esters followed by reaction of resulting glycosyl β-amino esters with diisocyanates. The developed sugar-based molecules were well characterized by extensive standard spectroscopic analysis including NMR (1H, 13C, and DEPT), IR, MS, and elemental analysis and were screened for their biological activity against Mycobacterium tuberculosis (M. Tb.), where some of them displayed potent antitubercular activity. The molecules have been designed keeping in view the well-known inhibitors of the enzymes involved in the biosynthesis of mycobacterial cell wall polymers and may be further explored as lead molecules for the successful development of a potential antitubercular drug candidate.Dedicated to Dr. Rama P. Tripathi, Former Chief Scientist at CSIR-Central Drug Research Institute, Lucknow, India, for his extraordinary contribution to “Drug development against Tuberculosis”

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