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

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

Uses

Used in Pharmaceutical Industry:
GEIPARVARIN is used as an enzyme inhibitor for its ability to suppress the activity of cytochrome P450 enzymes involved in drug metabolism. This application can lead to drug interactions and changes in the pharmacokinetics of co-administered medications, which may be beneficial in certain therapeutic contexts.
Used in Cancer Treatment Research:
In the field of oncology, GEIPARVARIN is being studied as a potential adjuvant therapy due to its demonstrated antitumor activity in preclinical studies. Its role in cancer treatment may involve enhancing the effectiveness of existing therapies or providing an alternative approach for managing cancer. Further research is necessary to understand its full therapeutic potential and any possible side effects associated with its use in cancer treatment.

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

• 98066-12-7 (+/-)-(E)-7-<<(3-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2-butenyl>-oxy>-2H-1-benzopyran-2-one 
• 35272-88-9 trans-1-acetoxy-3-methyl-2-penten-4-yne 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 85733-29-5 (E)-5-acetoxy-2,6-dimethyl-8-(2-oxo-2H-chromen-7-yloxy)-6-octen-3-yn-2-ol 
• 78957-34-3 7-((E)-4,7-Dihydroxy-3,7-dimethyl-oct-2-en-5-ynyloxy)-chromen-2-one 
• 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 
• 16851-02-8 2-[(2-oxo-2H-chromen-7-yl)oxy]acetaldehyde 
• 18458-23-6 2,2-dimethyl-5-ethyl-furan-3(2H)-one 
• 90995-08-7 7-<(2E)-7-bromo-4-diethylamino-3,7-dimethyl-6-oxo-octa-2,4-dienyloxy>coumarin 

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 [3+2] nitrile oxide intermolecular cycloaddition approach to 4,5-dihydro-3(2H)-furanone and 3(2H)-furanone ring systems: Application to the formal synthesis of (±)-ascofuranone and geiparvarin

A unified approach to both 4,5-dihydro-3(2H)-furanone and 3(2H)-furanone rings systems centered on a [3+2] nitrile oxide cycloaddition strategy as a tool for the crucial carbon-carbon bond forming step has been successfully applied to the formal synthesis of )(±)-ascofuranone and to a new synthesis of geiparvarin from common intermediates.

SIMPLE SYNTHETIC ROUTES TO GEIPARVARIN

Starting from geranyl acetate, efficient routes to 3(2H)-furanone derivatives via allylic oxidation and cyclization are described which have been utilized in the synthesis of a naturally occurring antitumor agent, geiparvarin.

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.

New geiparvarin analogues from 7-(2-oxoethoxy)coumarins as efficient in vitro antitumoral agents

A new class of compounds analogues of geiparvarin is described: aldolic condensation of 3(2H)-furanones and 7-(2-oxoethoxy)coumarins followed by a very efficient dehydration protocol led to the title compounds which show good antitumoral activity against several human cell lines.

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

New Syntheses of Geiparvarin and 2,5-Dimethyl-3(2H)-furanone via CO2 Mediated Bond Reorganization

A new synthesis of 3(2H)-furanones from 4-hydroxy-2-alkyn-1-one derivatives via CO2 mediated bond reorganization has been developed to the preparation of an antitumor agent, geiparvarin and a constituent of flavors, 2,5-dimethyl-3(2H)-furanone.

ISOXAZOLES-MEDIATED SYNTHESIS OF GEIPARVARIN AND DIHYDROGEIPARVARIN

A new synthesis of geiparvarin 1 and its dihydroderivative 2, two naturally occuring antitumor agents, possessing the 3(2H)-furanone ring system central structural feature, is described.The synthetic design is based on the use of suitably substituted isoxazole derivatives, the heterocyclic ring acting as masked 1,3-diketone moiety.

Total Syntheses of Fungal Metabolites and Functionalized Furanones

Simple, efficient syntheses of the fungal metabolites colletochlorin D and (+/-)-ascofuranone and one of its stereoisomers are described.Our investigations of functionalized furanones also enabled us to develop a nine-step (22percent overall yield) synthe