221054-70-2

Basic information

• Product Name: (5R)-5-ETHYL-5-HYDROXY-1,4,5,8-TETRAHYDROOXEPINO[3,4-C]PYRIDINE-3,9-DIONE
• Synonyms: (5R)-5-ETHYL-5-HYDROXY-1,4,5,8-TETRAHYDROOXEPINO[3,4-C]PYRIDINE-3,9-DIONE
• CAS NO: 221054-70-2
• Molecular Formula: C11H13 N O4
• Molecular Weight: 223.23
• Mol File: 221054-70-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5R)-5-ETHYL-5-HYDROXY-1,4,5,8-TETRAHYDROOXEPINO[3,4-C]PYRIDINE-3,9-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-5-ETHYL-5-HYDROXY-1,4,5,8-TETRAHYDROOXEPINO[3,4-C]PYRIDINE-3,9-DIONE(221054-70-2)
• EPA Substance Registry System: (5R)-5-ETHYL-5-HYDROXY-1,4,5,8-TETRAHYDROOXEPINO[3,4-C]PYRIDINE-3,9-DIONE(221054-70-2)

Safety Data

• Hazardous Substances Data: 221054-70-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
(5R)-5-Ethyl-5-hydroxy-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione is used as a potential pharmaceutical agent for [application reason] due to its unique structure and functional groups, which may offer novel interactions with biological targets.
Used in Chemical Research:
In the field of chemical research, (5R)-5-Ethyl-5-hydroxy-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione serves as a subject of study for [application reason], such as understanding its reactivity, stability, or potential to form new compounds with therapeutic properties.

Upstream product

• 250347-75-2 (R)-3-hydroxy-3-(3-hydroxymethyl-2-methoxypyridin-4-yl)pentanoic acid 
• 220998-02-7 (R)-3-(3-benzyloxymethyl-2-methoxypyridin-4-yl)-3-hydroxypentanoic acid 
• 186668-53-1 (+)-(5R)-5-Ethyl-5-hydroxy-1-methoxy-5.6-dihydro-9H-8-oxa-2-aza-benzocyclohepten-7-one 
• 500726-35-2 (+)-5-ethyl-5-hydroxy-1-methoxy-5,9-dihydro-8-oxa-2-aza-benzocyclohepten-7(6H)-one 
• 220998-01-6 3-(3-benzyloxymethyl-2-methoxy-pyridin-4-yl)-3-hydroxy-pentanoic acid 
• 472958-61-5 (R)-3-Hydroxy-3-(2-methoxy-3-methoxymethoxymethyl-pyridin-4-yl)-pentanoic acid 
• 472958-56-8 3-(2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl)pent-2-enoic acid ethyl ester 
• 472958-59-1 (+)-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pentane-1,3-diol 
• 472958-58-0 (+)-[3-ethyl-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]oxiran-2-yl]methanol 
• 472958-60-4 (-)-3-hydroxy-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pentanal 
• 472958-57-9 3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pent-2-en-1-ol 
• 472958-55-7 4-iodo-2-methoxy-3-(methoxymethoxymethyl)pyridine 
• 390824-46-1 (4-iodo-2-methoxypyridin-3-yl)-methanol 
• 158669-26-2 4-iodo-2-methoxynicotinaldehyde 

Downstream Products

• 220998-10-7 BN 80927 
• 220997-97-7 diflomotecan 

Relevant articles and documents

Practical racemic and asymmetric formal total syntheses of the homocamptothecin derivative and anticancer agent diflomotecan via tertiary homoallylic alcohols as masked aldol equivalents

An efficient and scalable racemic as well as an asymmetric approach to the key building block for the synthesis of homocamptothecin and derivatives thereof such as the potent anticancer agent diflomotecan (4) are described. In the asymmetric route, the pyridone ring was assembled applying straightforward carbonyl chemistry. The selective generation of the quaternary stereocenter was accomplished by self reproduction of chiral information starting from (S)-2-hydroxybutyric acid (22) utilizing an allyl moiety to act as a masked carbonyl group. The optically pure DE building block (7) (er > 99.95 : 0.05) was obtained in 9.0% overall yield over 10 steps (two chromatographic purifications). The asymmetric "de novo pyridone approach" has the potential to serve as the basis for a technical synthesis of diflomotecan.

Practical formal total syntheses of the homocamptothecin derivative and anticancer agent diflomotecan via asymmetric acetate aldol additions to pyridine ketone substrates

(Chemical Equation Presented) Two practical, efficient, and scalable asymmetric routes to DE ring fragment 7, a key building block in the synthesis of the homocamptothecin derivative diflomotecan 4, are described. The "acetal route" starts from 2-chloro-4

Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins

A method of synthesizing a compound having the formula: from a compound having the formula: wherein R1 is hydrogen, fluorine, chlorine or SiR5R6R7, wherein R5, R6, and R7 are independently the same or different an alkyl group or an aryl group, R2 is an alkyl group, R3 is a protecting group, R4 is an alkyl group, an allyl group, a propargyl group —CO2H, or a benzyl group, R8 is —CO2R10, wherein R10 is an alkyl group or an aryl group, X1 is OH and X2 is H, includes the step of exposing compound (III) to at least one of an organic acid or an inorganic acid. A compound has the general formula (III).

Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents.

Comptothecin analogues, preparation methods therefor, use thereof as drugs, and pharmaceutical compositions containing said analogues

The compound of the formula wherein the substituents are defined as in the specification and its non-toxic, pharmaceutically acceptable salts which are useful for the treatment of viral infections, parasitic diseases and the treatment of cancer.

Topoisomerase I-mediated antiproliferative activity of enantiomerically pure fluorinated homocamptothecins

Homocamptothecin (hCPT) is an E-ring modified camptothecin (CPT) analogue bearing a methylene spacer between the alcohol and carboxyl functions of the CPT lactone. Combining pronounced inhibitory activity of topoisomerase I (Topo I) with enhanced plasma s

BN 80927: A novel homocamptothecin with inhibitory activities on both topoisomerase I and topoisomerase II

BN 80927, a novel homocamptothecin derivative, inhibits both topoisomerase I and topoisomerase II mediated DNA relaxation and shows pronounced cytotoxicity against HT29, SKOV-3, DU145 and MCF7 human tumor cell lines.