36413-91-9

Basic information

• Product Name: GEIPARVARIN
• Synonyms: GEIPARVARIN;7-[[(E)-3-[(4,5-Dihydro-5,5-dimethyl-4-oxofuran)-2-yl]-2-butenyl]oxy]-2H-1-benzopyran-2-one;7-[[(E)-3-[(4-Oxo-5,5-dimethyl-4,5-dihydrofuran)-2-yl]-2-butenyl]oxy]-2H-1-benzopyran-2-one;GEIPARVARIN(RG)(CALL)
• CAS NO: 36413-91-9
• Molecular Formula: C19H18O5
• Molecular Weight: 326.34
• Product Categories: Coumarins
• Mol File: 36413-91-9.mol
• Article Data: 17

Chemical Properties

• Melting Point: 158-159 °C(Solv: methanol (67-56-1))
• Boiling Point: 533.1°Cat760mmHg
• Flash Point: 304.7°C
• Appearance: /
• Density: 1.242g/cm³
• Vapor Pressure: 1.92E-11mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: GEIPARVARIN(CAS DataBase Reference)
• NIST Chemistry Reference: GEIPARVARIN(36413-91-9)
• EPA Substance Registry System: GEIPARVARIN(36413-91-9)

Safety Data

• Hazardous Substances Data: 36413-91-9(Hazardous Substances Data)

Usage

General Description

GEIPARVARIN is a semi-synthetic chemical compound derived from a natural product and is classified as a furanocoumarin. It is primarily found in plants such as grapefruits and limes and is known for its ability to inhibit the activity of enzymes involved in drug metabolism, specifically cytochrome P450 enzymes. This inhibitory effect can lead to drug interactions and changes in the pharmacokinetics of co-administered medications. GEIPARVARIN has been studied for its potential use as an adjuvant therapy in cancer treatment, as it has shown antitumor activity in preclinical studies. However, further research is needed to fully understand its therapeutic potential and possible side effects.

InChI:InChI=1/C19H18O5/c1-12(15-11-17(20)19(2,3)24-15)8-9-22-14-6-4-13-5-7-18(21)23-16(13)10-14/h4-8,10-11H,9H2,1-3H3/b12-8+

Upstream product

• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 87064-12-8 5-<(E)-3-methanesulfonyloxy-1-methylpropenyl>-2,2-dimethylfuran-3(2H)-one 
• 92611-86-4 5-((E)-3-Bromo-1-methyl-propenyl)-2,2-dimethyl-furan-3-one 
• 35272-88-9 trans-1-acetoxy-3-methyl-2-penten-4-yne 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 14316-68-8 (E)-2-methyl-2-butenoic anhydride 
• 78957-34-3 7-((E)-4,7-Dihydroxy-3,7-dimethyl-oct-2-en-5-ynyloxy)-chromen-2-one 
• 78957-45-6 (E)-2-methyl-4-(2-oxo-2H-1-benzopyran-7-yloxy)but-2-enal 
• 89983-26-6 ethyl (+/-)-(E)-3-(6,6-dimethyl-1,4,7-trioxaspiro<4.4>non-8-yl)-2-butenoate 
• 93741-02-7 (+/-)-(E)-3-(6,6-dimethyl-1,4,7-trioxaspiro<4.4>non-8-yl)-2-buten-1-ol 
• 93741-03-8 (+/-)-(E)-8-(3-bromo-1-methyl-1-propenyl)-6,6-dimethyl-1,4,7-trioxaspiro<4.4>nonane 
• 89983-29-9 (+/-)-(E)-8-(3-chloro-1-methyl-1-propenyl)-6,6-dimethyl-1,4,7-trioxaspiro<4.4>nonane 
• 477934-88-6 2-(3-ethyl-5-isoxazolyl)-2-propanol 
• 115-19-5 2-methyl-but-3-yn-2-ol 

Relevant articles and documents

Natural and synthetic geiparvarins are strong and selective MAO-B inhibitors. Synthesis and SAR studies

Natural geiparvarin 1 and a number of its analogues were prepared and tested as inhibitors of both monoamine oxidase isoforms, MAO-B and MAO-A. The desmethyl congener 6 of geiparvarin, proved potent and selective MAO-B inhibitor (pIC50=7.55 vs 4.62). X-ray crystallography and molecular modelling studies helped the understanding of the observed structure-activity relationships.

A new nitrile oxide based synthesis of the antitumor agent Geiparvarin

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A CONVENIENT SYNTHESIS OF GEIPARVARIN

Acylation of 3-methyl-2,3-bis(trimethylsiloxy)-1-butene (PhLi) with (E)-2-methyl-2-butenoyl chloride gives the corresponding 3(2H)-furanone derivative, which can be readily converted to the naturally occurring antitumor agent Geiparvarin by two steps.

Geiparvarin analogues. 3. Synthesis and cytostatic activity of 3(2H)- furanone and 4,5-dihydro-3(2H)-furanone congeners of geiparvarin, containing a geraniol-like fragment in the side chain

Continuing our study on the structural features of geiparvarin (1), responsible for cytostatic activity, a series of 4,5-dihydro-3(2H)-furanones 10a-f and of 3(2H)-furanones 11a-f as well as 2'',3''-dihydrogeiparvarin (14) have been designed and synthesiz