19074-77-2

Basic information

• Product Name: (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester
• Synonyms: (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester;Minovin;Minovine
• CAS NO: 19074-77-2
• Molecular Formula: C22H28N2O2
• Molecular Weight: 352.46992
• Mol File: 19074-77-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester(19074-77-2)
• EPA Substance Registry System: (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester(19074-77-2)

Safety Data

• Hazardous Substances Data: 19074-77-2(Hazardous Substances Data)

Usage

Description

(5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester is an alkaloid derived from the plant Vinca minor L. It is potentially optically inactive, with a specific rotation reported as [α]D 00 ± 2° (c 1.0, EtOH). The ultraviolet spectrum in EtOH exhibits a broad absorption maximum at 338 mil and an inflexion at 310 mil. The structure of this compound has been confirmed through the synthesis of the (±)-form.

Uses

Used in Pharmaceutical Industry:
(5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester is used as a pharmaceutical compound for its potential therapeutic applications. The alkaloid's unique structure and properties make it a promising candidate for the development of new drugs and treatments.
Used in Chemical Research:
In the field of chemical research, (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester serves as a valuable subject for studying the properties and interactions of alkaloids. Its synthesis and structural confirmation contribute to the understanding of the chemical behavior of similar compounds and can lead to the discovery of new synthetic methods and applications.
Used in Drug Development:
(5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester is utilized in drug development as a starting material or a key intermediate for the synthesis of novel therapeutic agents. Its unique structural features can be exploited to design and develop new drugs with improved efficacy and selectivity.
Used in Quality Control and Standardization:
This alkaloid can be employed in the quality control and standardization of natural products and pharmaceuticals derived from Vinca minor L. or other related plants. By establishing a reference standard for (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester, it becomes possible to ensure the consistency, purity, and potency of related products in the market.

References

Kokry, Dubravkova, Sefecovic.,Experientia, 18,564 (1962)Mokryetal., ibid, 19,311 (1963)Zachystalova, Strouf, Trojanek., Chern. & Ind., 610 (1963)Synthesis: Kutney et al., J. Amer. Chern. Soc., 90,3891 (1968)

Upstream product

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Relevant articles and documents

Vincadifformine and minovine, 2 additional racemic alkaloids from Vinca minor L.

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Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids

A concise 11-step total synthesis of (-)- and ent-(+)-vindoline (3) is detailed based on a unique tandem intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole inspired by the natural product structure, in which three rings and four C-C bonds are formed central to the characteristic pentacyclic ring system setting all six stereocenters and introducing essentially all the functionality found in the natural product in a single step. As key elements of the scope and stereochemical features of the reaction were defined, a series of related natural products of increasing complexity were prepared by total synthesis including both enantiomers of minovine (4), 4-desacetoxy-6,7-dihydrovindorosine (5), 4-desacetoxyvindorosine (6), and vindorosine (7) as well as /V-methylaspidospermidine (11). Subsequent extensions of the approach provided both enantiomers of 6,7-dihydrovindoline (8), 4-desacetoxyvindoline (9), and 4-desacetoxy-6,7-dihydrovindoline (10).

Studies on indole alkaloid biosynthesis.

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