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Biomedical subjects

Hanbiao Yang

Publications and source records attributed to Hanbiao Yang.

5 recordsLinked to original sources

Surface-rolling molecules.

Design, syntheses, and testing of new, fullerene-wheeled single molecular nanomachines, namely, nanocars and nanotrucks, are presented. These nanovehicles are composed of three basic components that include spherical fullerene wheels, freely rotating alkynyl axles, and a molecular chassis. The use of spherical wheels based on C60 and freely rotating axles based on alkynes permits directed nanoscale rolling of the molecular structure on gold surfaces. The rolling motion observed by STM resembles the same motion performed by macroscopic entities in which rolling occurs perpendicular to the axles. A new synthesis methodology, in situ ethynylation of fullerenes, was developed for the realization of the fullerene-wheeled molecular machines. Four generations of the fullerene-wheeled structures were developed, and the latest fourth generation nanocar, 3b, along with three-wheeled triangular compounds, 4a and 4b, provided definitive evidence for fullerene-based wheel-like rolling motion, not stick-slip or sliding translation. The studies here underscore the ability to control directionality of motion in molecular-sized nanostructures through precise molecular design and synthesis.

Journal Article↗

A Ru-catalyzed tandem alkyne-enone coupling/Michael addition: synthesis of 4-methylene-2,6-cis-tetrahydropyrans.

[reaction: see text] A Ru-catalyzed tandem alkyne-enone coupling/Michael addition reaction is reported. It provides an efficient, atom-economic entry to 4-methylene-2,6-cis-tetrahydropyrans from simple, readily available homopropargylic alcohols and beta,gamma-unsaturated enones in good yields. Further functionalization of the resultant vinylsilane leads to the synthesis of either geometrically defined trisubstituted alkene exocyclic to the 2,6-cis-dihydropyran.

Alkenes↗

A formal synthesis of (-)-mycalamide A.

Novel strategies are developed for an efficient formal synthesis of (-)-mycalamide A. The left-hand side (-)-7-benzoylpederic acid is synthesized from (2S,3S)-2,3-epoxybutane. The key features include a highly regioselective Ru-catalyzed alkene-alkyne coupling reaction and a novel way to control the challenging C(7) stereocenter. The right-hand side was synthesized from (R)-pantolactone. The complex trioxodecalin core is constructed with two Pd(0)-catalyzed O-pi-allyl cyclizations. The first one is chemoselective, while the second one is highly diastereoselective. Three additional steps would be required to complete a total synthesis of (-)-mycalamide A.

Animals↗

Novel prodrug approach to amprenavir-based HIV-1 protease inhibitors via O-->N acyloxy migration of P1 moiety.

We have developed a new approach to prodrugs, which utilizes a pH-induced intramolecular O-->N migration of an acyloxy group in carbonate moiety to a free amino moiety at neutral pH. This method is exemplified by facile rearrangement of highly water-soluble prodrug 3 to carbamate 4, a close analogue of HIV-1 protease inhibitor Amprenavir. The O-->N acyloxy migration is unprecedented in the context of prodrugs and it enables a high atom economy due to recycling of the 'pro' moiety.

Carbamates↗

Recent progress in discovery of small-molecule CCR5 chemokine receptor ligands as HIV-1 inhibitors.

This review addresses key pharmacology and virology issues relevant in discovery and development of CCR5 antagonists as anti-HIV drugs, such as target validation, receptor internalization, allosterism, viral resistance and tropism. Recent progress in the discovery and development of CCR5 antagonists, SAR and clinical status are reviewed. Finally, modeling-based structure of CCR5 is discussed in the context of a small-molecule antagonism of the CCR5 receptor.

Animals↗