36804-95-2

Usage

Uses

Used in Pharmaceutical Industry:
Deoxyharringtonine is used as a chemotherapeutic agent for its potential anticancer properties. It is particularly effective against leukemia and solid tumors, as it disrupts the translation process in cancer cells, leading to cell death.
Used in Cancer Research:
Deoxyharringtonine is used as a subject of study in cancer research to further understand its mechanisms of action and optimize its use in cancer treatment. Early clinical trials have shown promising results, and additional research is needed to fully comprehend its potential and effectiveness in treating various types of cancer.

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

• 910138-94-2 (-)-deoxyharringtonine β-lactone 
• 124-41-4 sodium methylate 
• 864081-87-8 (2R,4R)-[2-tert-butyl-4-(3-methylbut-2-enyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid 
• 910138-83-9 C₂₀H₂₃NO₅ 
• 24316-19-6 cephalotaxine 
• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 32583-40-7 [[1-methoxy-2-(trimethylsilyl)ethenyl]oxy]trimethylsilane 
• 26395-06-2 5-methyl-2-oxo-hexanoic acid 
• 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 
• 910138-87-3 C₃₀H₃₃NO₉ 

Relevant academic research and scientific papers

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.

Diastereoselective Synthesis of Cephalotaxus Esters via Asymmetric Mukaiyama Aldol Reaction

We report a protocol for efficient stereoselective installation of the chiral oxygen-containing tetrasubstituted tertiary carbon stereocenter of the side chain of cephalotaxus esters by means of highly diastereoselective Mukaiyama aldol reactions between α-keto esters (2) and a (Z)-α-chloro ketene silyl acetal. This protocol permitted synthesis of cephalotaxus esters including six natural products in good to excellent yields (up to 94%) with high diastereoselectivities (dr up to 97:3) and could be performed on a multigram scale.

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.

Synthesis of antiproliferative cephalotaxus esters and their evaluation against several human hematopoietic and solid tumor cell lines: Uncovering differential susceptibilities to multidrug resistance

Deoxyharringtonine (2), homoharringtonine (3), homodeoxyharringtonine (4), and anhydroharringtonine (5) are reported to be among the most potent members of the antileukemia alkaloids isolated from the Cephalotaxus genus. Convergent syntheses of these four natural products are described, each involving novel synthetic methods and strategies. These syntheses enabled evaluation of several advanced natural and non-natural compounds against an array of human hematopoietic and solid tumor cells. Potent cytotoxicity was observed in several cell lines previously not challenged with these alkaloids. Variations in the structure of the ester chain within this family of alkaloids confer differing activity profiles against vincristine-resistant HL-60/RV+, signalling new avenues for molecular design of these natural products to combat multi-drug resistance.

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