26833-85-2

Basic information

• Product Name: HARRINGTONINE
• Synonyms: (3(r))-ter;4-methyl-cephalotaxin2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioate(es;alkaloidcfromcephalotaxus;cephalotaxine,4-methyl(2r)-2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioat;nsc124147;HARRINGTONIN;HARRINGTONINE;HT
• CAS NO: 26833-85-2
• Molecular Formula: C28H37NO9
• Molecular Weight: 531.59
• Product Categories: Alkaloids;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 26833-85-2.mol

Chemical Properties

• Melting Point: 73～75℃
• Boiling Point: 679.419 °C at 760 mmHg
• Flash Point: 364.7 °C
• Appearance: white solid
• Density: 1.35 g/cm³
• Vapor Pressure: 2.17E-19mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: 2-8°C
• PKA: 11.62±0.29(Predicted)
• CAS DataBase Reference: HARRINGTONINE(CAS DataBase Reference)
• NIST Chemistry Reference: HARRINGTONINE(26833-85-2)
• EPA Substance Registry System: HARRINGTONINE(26833-85-2)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 26833-85-2(Hazardous Substances Data)

Usage

Uses

Used in Oncology:
Harringtonine is used as a specific anti-leukemia drug for its significant antitumor activities. It is particularly effective against chronic myelogenous leukemia, where it has shown promising results in mitigating the disease.
Used in Cancer Treatment:
Harringtonine is used as a natural product with significant antitumor activities in cancer treatment. Its ability to inhibit protein synthesis and immobilize ribosomes makes it a valuable compound in the development of novel therapeutic strategies against various types of cancer.
Used in Translational Research:
Harringtonine is used as a tool to capture ribosome-protected mRNA fragments for evaluating translation. Its ability to immobilize initiating ribosomes can provide valuable insights into the process of translation and help researchers better understand the molecular mechanisms underlying various diseases, including cancer.

References

Mikolajczak, Powell, Smith, Tetrahedron, 28, 1995 (1972) Kelly, McKenna, Christenson, Tetrahedron Lett., 35m (1973)

InChI:InChI=1/C28H37NO9/c1-26(2,32)8-9-28(33,15-22(30)35-4)25(31)38-24-21(34-3)14-27-7-5-10-29(27)11-6-17-12-19-20(37-16-36-19)13-18(17)23(24)27/h12-14,23-24,32-33H,5-11,15-16H2,1-4H3/t23-,24-,27+,28-/m1/s1

Upstream product

• 68423-52-9 (Ξ)-2-benzyloxy-2-(3-hydroxy-3-methyl-butyl)-succinic acid 1-((3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester 
• 68423-50-7 4-benzyloxy-7,7-dimethyl-2-oxo-oxepane-4-carbonyl chloride 
• 68423-51-8 (Ξ)-4-benzyloxy-7,7-dimethyl-2-oxo-oxepane-4-carboxylic acid (3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl ester 
• 24316-19-6 cephalotaxine 

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.

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.