174092-78-5

Basic information

• Product Name: (S)-4-Ethyl-4-hydroxy-8-Methoxy-6-triMethylsilanyl-1,4-dihydro-pyrano[3,4-c]pyridin-3-one
• Synonyms: (S)-4-Ethyl-4-hydroxy-8-Methoxy-6-triMethylsilanyl-1,4-dihydro-pyrano[3,4-c]pyridin-3-one
• CAS NO: 174092-78-5
• Molecular Formula: C14H21NO4Si
• Molecular Weight: 295.40634
• Mol File: 174092-78-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-4-Ethyl-4-hydroxy-8-Methoxy-6-triMethylsilanyl-1,4-dihydro-pyrano[3,4-c]pyridin-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Ethyl-4-hydroxy-8-Methoxy-6-triMethylsilanyl-1,4-dihydro-pyrano[3,4-c]pyridin-3-one(174092-78-5)
• EPA Substance Registry System: (S)-4-Ethyl-4-hydroxy-8-Methoxy-6-triMethylsilanyl-1,4-dihydro-pyrano[3,4-c]pyridin-3-one(174092-78-5)

Safety Data

• Hazardous Substances Data: 174092-78-5(Hazardous Substances Data)

Usage

General Description

(S)-4-Ethyl-4-hydroxy-8-Methoxy-6-triMethylsilanyl-1,4-dihydro-pyrano[3,4-c]pyridin-3-one is a chemical compound with a complex molecular structure. It contains an ethyl group, hydroxy group, methoxy group, and trimethylsilyl group, along with a pyrano[3,4-c]pyridin-3-one ring system. (S)-4-Ethyl-4-hydroxy-8-Methoxy-6-triMethylsilanyl-1,4-dihydro-pyrano[3,4-c]pyridin-3-one is a derivative of pyrano[3,4-c]pyridine and has potential pharmaceutical applications due to its unique structure and properties. The presence of functional groups like hydroxy and methoxy make it potentially useful for medicinal chemistry, and its structural complexity suggests that it may have interesting biological activity. Further research and evaluation of this compound could yield valuable insights into its potential uses in the pharmaceutical industry.

Upstream product

• 453518-24-6 (S)-4-ethyl-3,4-dihydro-3,4-dihydroxy-8-methoxy-6-trimethylsilyl-1H-pyrano[3,4-c] pyridine 
• 453518-21-3 2-Methoxy-6-trimethylsilanyl-pyridine-3-carbaldehyde 
• 174092-76-3 3-(2-butenyloxymethyl)-4-iodo-2-methoxy-6-trimethylsilylpyridine 
• 174092-75-2 4-iodo-2-methoxy-6-trimethylsilanyl-3-pyridinecarboxaldehyde 
• 170453-55-1 2-methoxy-6-(trimethylsilyl)pyridine 
• 40473-07-2 6-bromo-2-methoxypyridine 
• 174092-77-4 4-Ethyl-8-methoxy-6-trimethylsilanyl-1H-pyrano[3,4-c]pyridine 

Downstream Products

• 149882-10-0 lurtotecan 
• 7689-03-4 camptothecin 
• 86639-52-3 7-ethyl-10-hydroxycamptothecin 
• 19685-10-0 10-methoxycamptothecin 
• 19685-09-7 (S)-10-hydroxycamptothecin 
• 110351-92-3 (R)-4-ethyl-4-hydroxy-1,12-dihydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H)-dione 
• 828934-85-6 (R)-(-)-20-fluorocamptothecin 
• 174092-79-6 (S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one 

Relevant articles and documents

Total and semisynthesis and in vitro studies of both enantiomers of 20-fluorocamptothecin

Both enantiomers of 20-fluorocamptothecin and the racemate have been prepared by total synthesis. The (R)-enantiomer is essentially inactive in a topoisomerase-I/DNA assay, while the (S)-enantiomer is much less active than (20S)-camptothecin. The lactone ring of 20-fluorocamptothecin hydrolyzes more rapidly than that of camptothecin in PBS. The results provide insight into the role of the 20-hydroxy group in the binding of camptothecin to topoisomerase-I and DNA.

A general synthetic approach to the (20s)-camptothecin family of antitumor agents by a regiocontrolled cascade radical cyclization of aryl isonitriles

A general and efficient synthesis of (20S)-camptothecin (1a) is reported. A key common intermediate containing the pyridone and lactone (DE) rings of camptothecin and most derivatives was constructed from 2-trimethylsilyl-6-methoxypyridine by a series of metalation reactions and a Heck cyclization to provide an achiral bicyclic enol ether. Sharpless asymmetric dihydroxylation followed by lactol oxidation and iododesilylation produced the key intermediate in 94% enantiomeric excess. Alkylation with prop-argyl bromide and a cascade radical reaction with phenyl isonitrile then produced 1a. About 20 other penta-and hexacyclic analogues of camptothecin with differing single or multiple substituents at C7, C9, C10, C11, and/or C12 were made by changing the propargylating agent and the isonitrile. Included among these are several drug candidates and the approved drugs topotecan and irinotecan. The synthesis of the prodrug irinotecan is a direct one that does not pass through the active metabolite. The use of ortho-trimethylsilyl-substituted isonitriles allows the regioselective synthesis of camptothecin analogues in cases where isomeric mixtures are formed from the parent isonitriles. The synthesis of the derivatives relies on the broad scope and functional group tolerance of the key cascade radical reaction.