36804-95-2

Basic information

• Product Name: Deoxyharringtonine
• Synonyms: Deoxyharringtonine;(2R)-2-Hydroxy-2-(methoxycarbonyl)methyl-5-methylhexanoic acid (1S,3aR)-1,5,6,8,9,14bβ-hexahydro-2-methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-yl ester
• CAS NO: 36804-95-2
• Molecular Formula: C28H37NO8
• Molecular Weight: 515.599
• Mol File: 36804-95-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 645.8°Cat760mmHg
• Flash Point: 344.4°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 1.46E-17mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: Deoxyharringtonine(CAS DataBase Reference)
• NIST Chemistry Reference: Deoxyharringtonine(36804-95-2)
• EPA Substance Registry System: Deoxyharringtonine(36804-95-2)

Safety Data

• Hazardous Substances Data: 36804-95-2(Hazardous Substances Data)

Usage

General Description

Deoxyharringtonine is a natural compound extracted from the Cephalotaxus harringtonia plant, and it is commonly used as a chemotherapeutic agent. It belongs to the family of alkaloids and is known for its ability to inhibit protein synthesis in cancer cells. Deoxyharringtonine has been studied for its potential anticancer properties and has shown promising results in early clinical trials for the treatment of various types of cancer, including leukemia and solid tumors. The compound is believed to work by disrupting the translation process in cancer cells, ultimately leading to cell death. However, further research is needed to fully understand its mechanisms of action and to optimize its use in cancer treatment.

InChI:InChI=1/C28H37NO8/c1-17(2)6-9-28(32,15-23(30)34-4)26(31)37-25-22(33-3)14-27-8-5-10-29(27)11-7-18-12-20-21(36-16-35-20)13-19(18)24(25)27/h12-14,17,24-25,32H,5-11,15-16H2,1-4H3/t24-,25-,27+,28-/m1/s1

Upstream product

• 910138-78-2 6-[2-(benzo[1,3]dioxol-5-yl)aziridin-1-yl]-2,2-dimethyl-3a,6a-dihydrocyclopenta[1,3]dioxol-4-one 
• 910138-91-9 (-)-2-hydroxy-2-(3-methylbut-2-enyl)succinic acid 1-benzyl ester 
• 910138-75-9 (+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[1,3]dioxol-4-ol 
• 910138-92-0 2-(3-methyl-but-2-enyl)-4-oxo-oxetane-2-carboxylic acid benzyl ester 
• 910138-93-1 (+)-2-(3-methylbutyl)-4-oxooxetane-2-carboxylic acid 
• 910138-76-0 (-)-6-chloro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol 
• 1040271-76-8 6-chloro-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 864081-87-8 (2R,4R)-[2-tert-butyl-4-(3-methylbut-2-enyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid 
• 910138-94-2 (-)-deoxyharringtonine β-lactone 
• 124-41-4 sodium methylate 
• 54086-34-9 2-[3-Methyl-but-(Z)-ylidene]-succinic acid dimethyl ester 
• 590-86-3 isovaleraldehyde 
• 90613-19-7 isopentylidene-succinic acid 
• 62681-68-9 1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one oxime 

Relevant articles and documents

Synthesis method and intermediate of ester derivative of (-)-cephalotaxine

The invention discloses a synthesis method and an intermediate of an ester derivative of (-)-cephalotaxine. The synthesis method is characterized in that a compound A and a compound 4 undergoes a condensation reaction shown in the description in a solvent under the action of a condensing agent in order to obtain a compound I. The synthetic method utilizes an esterification reaction of a racemic epoxy branched-chain compound and the (-)-cephalotaxine to highly selectively obtain the chiral compound close to a single configuration, so the method has the advantages of simple and mild synthesis route, and easiness in industrialization.

CEPHALOTAXUS ESTERS, METHODS OF SYNTHESIS, AND USES THEREOF

The present invention provides novel cephalotaxus esters, syntheses thereof, and intermediates thereto. The invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of using said compounds or compositions in the treatment of proliferative diseases (e.g., benign neoplasm, cancer, inflammatory disease, autoimmune disease, diabetic retinopathy) and infectious disease. The invention further provides methods of using said compounds or compositions in the treatment of multidrug resistant cancer.

Strain-release rearrangement of N-vinyl-2-arylaziridines. Total synthesis of the anti-leukemia alkaloid (-)-deoxyharringtonine

Deoxyharringtonine (1) is among the most potent of the anti-leukemia alkaloids isolated from the Cephalotaxus genus. A convergent total synthesis of (-)-1 is reported, involving novel synthetic methods and strategies that include (1) the strain-release rearrangement of N-aryl-2-vinylaziridines for [3]benzazepine synthesis, (2) a vinylogous amide acylation-cycloaddition cascade for spiro-pyrrolidine construction, and (3) efficient acylation of the cephalotaxine core by α-(β-lactone)carboxylic acid derivatives to access the biologically active cephalotaxus esters. These innovations should allow rapid access not only to other Cephalotaxus alkaloids but also to non-natural analogues of potential therapeutic utility. Copyright