182491-21-0 Usage
Description
4-Phenyltetrahydropyran-4-carboxylic acid is an organic compound that serves as a key intermediate in the synthesis of various pharmaceutical compounds, particularly imidazole-containing benzodiazepines and their analogs. It features a tetrahydropyran ring fused with a phenyl group and a carboxylic acid functional group, which contributes to its reactivity and potential applications in medicinal chemistry.
Uses
Used in Pharmaceutical Industry:
4-Phenyltetrahydropyran-4-carboxylic acid is used as a starting material for the preparation of imidazole-containing benzodiazepines and analogs. These compounds are of significant interest due to their potential therapeutic applications, including the treatment of various disorders and diseases. The synthesis of these bioactive molecules often involves the use of 4-phenyltetrahydropyran-4-carboxylic acid as a key building block, highlighting its importance in the development of new pharmaceutical agents.
Check Digit Verification of cas no
The CAS Registry Mumber 182491-21-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,2,4,9 and 1 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 182491-21:
(8*1)+(7*8)+(6*2)+(5*4)+(4*9)+(3*1)+(2*2)+(1*1)=140
140 % 10 = 0
So 182491-21-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H14O3/c13-11(14)12(6-8-15-9-7-12)10-4-2-1-3-5-10/h1-5H,6-9H2,(H,13,14)
182491-21-0Relevant articles and documents
Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class i HDAC Enzymes and Cancer Cell Proliferation
Tng, Jiahui,Lim, Junxian,Wu, Kai-Chen,Lucke, Andrew J.,Xu, Weijun,Reid, Robert C.,Fairlie, David P.
supporting information, p. 5956 - 5971 (2020/06/05)
AR-42 is an orally active inhibitor of histone deacetylases (HDACs) in clinical trials for multiple myeloma, leukemia, and lymphoma. It has few hydrogen bond donors and acceptors but is a chiral 2-arylbutyrate and potentially prone to racemization. We report achiral AR-42 analogues incorporating a cycloalkyl group linked via a quaternary carbon atom, with up to 40-fold increased potency against human class I HDACs (e.g., JT86, IC50 0.7 nM, HDAC1), 25-fold increased cytotoxicity against five human cancer cell lines, and up to 70-fold less toxicity in normal human cells. JT86 was ninefold more potent than racAR-42 in promoting accumulation of acetylated histone H4 in MM96L melanoma cells. Molecular modeling and structure-activity relationships support binding to HDAC1 with tetrahydropyran acting as a hydrophobic shield from water at the enzyme surface. Such potent inhibitors of class I HDACs may show benefits in diseases (cancers, parasitic infections, inflammatory conditions) where AR-42 is active.
