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Synthesis of the Naturally Occurring (-)-1,3,5-Tri-O-Caffeoylquinic Acid.

ABSTRACT: Ribonuclease H (RNase H) is an essential component to the replication of human immunodeficiency virus (HIV), and only a few inhibitors of this enzyme are known. Millenia Hope Pharmaceuticals Inc. found that (-)-1,3,5-tri-O-caffeoylquinic acid is a potent RNase H inhibitor and antiviral agent. A facile route leading to this inhibitor from commercially available (-)-quinic acid is reported within.

SUBMITTER: Brummond KM

PROVIDER: S-EPMC2778492 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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Synthesis of the Naturally Occurring (-)-1,3,5-Tri-O-Caffeoylquinic Acid.

Brummond Kay M KM Deforrest Jolie E JE

Synlett : accounts and rapid communications in synthetic organic chemistry 20090201

Ribonuclease H (RNase H) is an essential component to the replication of human immunodeficiency virus (HIV), and only a few inhibitors of this enzyme are known. Millenia Hope Pharmaceuticals Inc. found that (-)-1,3,5-tri-O-caffeoylquinic acid is a potent RNase H inhibitor and antiviral agent. A facile route leading to this inhibitor from commercially available (-)-quinic acid is reported within. ...[more]

PMID: 20157344

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Naturally Occurring Nervonic Acid Ester Improves Myelin Synthesis by Human Oligodendrocytes.

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Synthesis and structure of 2,4,6-tri-cyclo-butyl-1,3,5-trioxane.

Project description:The synthesis and structure of 2,4,6,-tri-cyclo-butyl-1,3,5-trioxane, C15H24O3 1, is described. It was formed in 39% yield during the work-up of the Swern oxidation of cyclo-butyl-methanol and may serve as a stable precursor of the cyclo-butane carbaldehyde. The mol-ecule of 1 occupies a special position (3.m) located at the center of its 1,3,5-trioxane ring. The latter is in a chair conformation, with the symmetry-independent O and C atoms deviating by 0.651 (4) Å from the least-squares plane of the other atoms of the trioxane ring. All three cyclo-butane substituents, which have a butterfly conformation with an angle between the two planes of 25.7 (3)°, are in the cis conformation relative to the 1,3,5-trioxane ring. Inter-molecular C-H⋯O inter-actions between the 1,3,5-trioxane rings consolidate the crystal structure, forming stacks along the c-axis direction. The crystal studied was refined a as a racemic twin.

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Total Synthesis of Naturally Occurring 5,7,8-Trioxygenated Homoisoflavonoids.

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3,4,5-Tri-O-Caffeoylquinic Acid Promoted Hair Pigmentation Through β-Catenin and Its Target Genes.

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Crystal structure of benzene-1,3,5-tri-carb-oxy-lic acid-4-pyridone (1/3).

Project description:Slow co-crystallization of a solution of benzene-1,3,5-tri-carb-oxy-lic acid with a large excess of 4-hy-droxy-pyridine produces an inter-penetrating, three-dimensional, hydrogen-bonded framework consisting of three 4-pyridone and one benzene-1,3,5-tri-carb-oxy-lic acid mol-ecules, C9H6O6·3C5H5NO. This structure represents an ortho-rhom-bic polymorph of the previously reported C-centered, monoclinic structure [Campos-Gaxiola et al. (2014 ▸). Acta Cryst. E70, o453-o454].

| S-EPMC4644998 | biostudies-literature

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