23360-92-1

Basic information

• Product Name: LEUROSINE
• Synonyms: LEUROSINE;4’-deoxy-3’,4’-epoxy-,(3’-alpha,4’-alpha)-vincaleukoblastin;4’-deoxy-3’,4’-epoxy-,(3’alpha,4’alpha)-vincaleukoblastin;amotin;nsc-528004;Vinleurosine;4b-Acetoxy-3,4epoxy-3-hydroxy-16-methoxy-(4 H)-vincaleukoblast-6-ene-23,22dioic Acid Dimethyl Ester;(3'R,4'S)-3',4'-Oxy-4'-deoxyvincaleukoblastine
• CAS NO: 23360-92-1
• Molecular Formula: C₄₆H₅₆N₄O₉
• Molecular Weight: 808.96
• Mol File: 23360-92-1.mol

Chemical Properties

• Melting Point: 202-205℃
• Appearance: /
• Density: 1.39
• Refractive Index: 1.677
• PKA: 11.36±0.60(Predicted)
• CAS DataBase Reference: LEUROSINE(CAS DataBase Reference)
• NIST Chemistry Reference: LEUROSINE(23360-92-1)
• EPA Substance Registry System: LEUROSINE(23360-92-1)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 23360-92-1(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
LEUROSINE is used as an antitumor compound for its antineoplastic properties. It is derived from Vinca Rosea, a plant known for its cancer-fighting abilities. LEUROSINE plays a crucial role in the treatment of various types of cancer by targeting and inhibiting the growth of cancer cells.
Used in Pharmaceutical Industry:
LEUROSINE is used as an active pharmaceutical ingredient for the development of cancer treatments. Its unique properties and origin from a natural source make it a valuable component in the creation of new drugs and therapies aimed at combating cancer.
Used in Research and Development:
LEUROSINE is used as a research compound for studying the mechanisms of action and potential applications in cancer treatment. Its complex structure and alkaloid nature provide valuable insights into the development of new antineoplastic agents and understanding the interactions between natural compounds and cancer cells.

References

Svoboda., J. Amer. Pharm. Assoc., 47,834 (1959) Neuss et al., J. Amer. Chern. Soc., 81,4754 (1959) Revised structure: Neuss et al., Tetrahedron Lett., 783 (1968)

InChI:InChI=1/C46H56N4O9/c1-8-42-16-12-18-50-20-17-44(37(42)50)30-21-31(34(55-5)22-33(30)48(4)38(44)46(54,41(53)57-7)39(42)58-26(3)51)45(40(52)56-6)23-27-24-49(25-43(9-2)36(27)59-43)19-15-29-28-13-10-11-14-32(28)47-35(29)45/h10-14,16,21-22,27,36-39,47,54H,8-9,15,17-20,23-25H2,1-7H3/t27-,36-,37+,38-,39-,42-,43+,44-,45+,46+/m1/s1

Upstream product

• 38390-45-3 anhydrovinblastine 
• 2468-21-5 catharinthine 
• 2182-14-1 vindoline 
• 26251-91-2 18(R)-methoxycarbonylcleavamine 

Downstream Products

• 54022-49-0 22-Oxoleurosin 
• 38390-45-3 anhydrovinblastine 
• 39608-80-5 pleurosine 

Relevant articles and documents

Synthesis of anti-tumor dimeric indole alkaloids in catharanthus roseus was promoted by irradiation with near-ultraviolet light at low temperature

We have found that coupling between catharanthine and vindoline occurs non-enzymatically in the presence of flavin mononucleotide and manganese ions with near- ultraviolet light irradiation in vitro. The present study found that the concentrations of cath

ALKALOID PRODUCTION IN CATHARANTHUS ROSEUS (L.) G. DON CELL CULTURES. XVI. BIOTRANSFORMATION OF 3',4'-ANHYDROVINBLASTINE WITH CATHARANTHUS ROSEUS CELL CULTURES AND ENZYME SYSTEMS

Employing cell cultures of Catharanthus roseus and enzyme systems derived from such cultures, a detailed study of the biotransformation of 3',4'-anhydrovinblastine (3) is described.It is shown that enzymatic conversion of 3 to the isolated end products, the bisindole alkaloids leurosine (4), vinblastine (5), catharine (6), vinamidine (7) and hydroxyvinamidine (8) proceeds initially to the same dihydropyridinium intermediate (9) obtained when the monomeric alkaloids catharanthine (1) and vindoline (2) are enzymatically coupled.These data establish that the overall biosynthetic pathway to the bisindole alkaloids proceeds from 1 and 2 to the initially formed 9 and the latter, under enzymatically controlled oxidation-reduction, affords the alkaloids 3-8.However, when 3 is incubated as substrate, the enzymes are capable of utilizing and converting it into the alkaloids 4-8.In summary, 3 is not a direct biosynthetic precursor of 4-8.

ALKALOID PRODUCTION IN CATHARANTHUS ROSEUS (L.) G. DON CELL CULTURES. XIV. THE ROLE OF UNSTABLE DIHYDROPYRIDINIUM INTERMEDIATES IN THE BIOSYNTHESIS OF BISINDOLE ALKALOIDS

Employing enzyme systems obtained from Catharanthus roseus cell cultures, experiments relating to the biosynthesis of various bisindole alkaloids are described.Specifically, the enzyme-catalyzed coupling of catharanthine (1) and vindoline (2) to a highly unstable dihydropyridinium intermediate (9), important in the biosynthesis of 3',4'-anhydrovinblastine (3), leurosine (4), catharine (6), vinamidine (7) and hydroxyvinamidine (8) is presented.Conversions of 9 to these alkaloids and its role in the biosynthesis is discussed.Although catharanthine is well utilized by the enzyme system, catharanthine N-oxide (10), an important intermediate in the chemical coupling of 1 and 2 to afford 9, is not utilized.

ALKALOID PRODUCTION IN CATHARANTHUS ROSEUS (L.) G. DON CELL CULTURES, XV. SYNTHESIS OF BISINDOLE ALKALOIDS BY USE OF IMMOBILIZED ENZYME SYSTEMS

Affinity gel bound enzyme systems obtained from Catharanthus roseus cell cultures were employed to establish a high yielding enzymatic system for the coupling of catharanthine (1) and vindoline (2) to 3',4'-anhydrovinblastine (3) and leurosine (4).Long term enzymatic activity can be preserved by this technique, an aspect which may prove important in subsequent utilization of such systems in large scale production.