Topic
Bicyclic molecule
About: Bicyclic molecule is a research topic. Over the lifetime, 29587 publications have been published within this topic receiving 451252 citations. The topic is also known as: bicyclic molecule.
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TL;DR: A new methodology for the synthesis of bicyclic peptides by using a reconstituted cell-free translation system under the reprogrammed genetic code offers a powerful means of mRNA-programmed synthesis of various peptides with uniform bicyclic scaffolds.
Abstract: Here we report a new methodology for the synthesis of bicyclic peptides by using a reconstituted cell-free translation system under the reprogrammed genetic code. Cysteine (Cys) and three different nonproteinogenic amino acids, Cab, Aha, and Pgl, were simultaneously incorporated into a peptide chain. The first cyclization occurred between the chloroacetyl group of Cab and the sulfhydryl group in Cys in situ of translation, and the second cyclization on the side chains of Aha−Pgl via Cu(I)-catalyzed azide−alkyne cycloaddition was performed. This offers us a powerful means of mRNA-programmed synthesis of various peptides with uniform bicyclic scaffolds.
115 citations
TL;DR: A decarboxylative ring-opening of the products led to the facile synthesis of vicinal biheteroaryls and a series of structurally diverse bicyclic or tricyclic compounds bearing an exocyclic double bond were constructed in good to excellent efficiency.
Abstract: Heteroarenes are important structural motif in functional molecules. Reported herein is a Mn(I)-catalyzed 1,2-diheteroarylation of allenes via a C-H activation/Smiles rearrangement cascade. The reaction occurred under additive-free or even solvent-free conditions which allowed the creation of two C-C and one C-N bonds in a single operation. A series of structurally diverse bicyclic or tricyclic compounds bearing an exocyclic double bond were constructed in good to excellent efficiency. The decarboxylative ring-opening of the products led to the facile synthesis of vicinal biheteroaryls. Synthetic applications were demonstrated and preliminary mechanistic studies were conducted.
114 citations
TL;DR: The efficient synthesis of novel azetidin-2-ones 6 has been established and structures of the synthesized compounds have been elucidated on the basis of their elemental analyses and spectral data.
114 citations
114 citations
TL;DR: Replacement of the substituted aryl moiety with various substituted indoles provided bis(heteroaryl)piperazines (BHAPs) that were 10-100-fold more potent than U-80493E.
Abstract: A variety of analogues of 1-[4-methoxy-3,56-dimethylbenzyl]-4-[3-(ethylamino)-2-pyridyl]piperazine hydrochloride (U-80493E) were synthesized and evaluated for their inhibition of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT). Replacement of the substituted aryl moiety with various substituted indoles provided bis(heteroaryl) piperazines (BHAPs) that were 10-100-fold more potent than U-80493E. The pyridyl portion of the lead molecule was found to be very sensitive to modifications. Extensive preclinical evaluations of several of these compounds led to the selection of 1-[(5-methoxyindol-2-yl)carbonyl]-4-[3-(ethylamino)-2-pyridyl]piperazine methanesulfonate (U-87201E, atevirdine mesylate) for clinical evaluation
114 citations