1857-30-3

Basic information

• Product Name: (+)-Viroallosecurinine
• Synonyms: (+)-Viroallosecurinine;(7R,9R)-Securinan-11-one;Alkaloid PN-A;Viroallosecurinine;Nsc326131
• CAS NO: 1857-30-3
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.2637
• Mol File: 1857-30-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 145-147℃ (hexane acetone )
• Boiling Point: 459°Cat760mmHg
• Flash Point: 197°C
• Appearance: /
• Density: 1.3g/cm³
• PKA: 8.29±0.20(Predicted)
• CAS DataBase Reference: (+)-Viroallosecurinine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Viroallosecurinine(1857-30-3)
• EPA Substance Registry System: (+)-Viroallosecurinine(1857-30-3)

Safety Data

• Hazardous Substances Data: 1857-30-3(Hazardous Substances Data)

Usage

General Description

(+)-Viroallosecurinine is a natural alkaloid compound that has been isolated from the plant Alstonia macrophylla. It belongs to the securinine type of alkaloids and has been found to exhibit various biological activities, including antiplasmodial and cytotoxic properties. Studies have shown that (+)-Viroallosecurinine has potent activity against the malaria parasite Plasmodium falciparum, making it a potential candidate for the development of new antimalarial drugs. Additionally, it has also shown promising cytotoxic activity against cancer cell lines, indicating its potential for further exploration as an anticancer agent. The compound's unique chemical structure and biological activities make it an interesting target for further research in the fields of medicine and pharmacology.

Upstream product

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• 708260-76-8 tert-butyl (2R)-2-[(2S)-2-[(Z)-4-iodo-3-butenyl]-5(2H)-oxo-2-furyl]piperidine-1-carboxylate 
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• 651737-98-3 1(S)-[(2'R)-N-tert-butoxycarbonylpiperidinyl]-1-ethynyl-4(Z)-hepten-1-ol 
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• 651737-96-1 1(S)-[(2''R)-N-tert-butoxycarbonylpiperidinyl]-1-(2'-trimethylsilylethynyl)-4(Z)-hepten-1-ol 
• 1126784-60-8 (1'S,3'S,8a'R)-3'-((Z)-2-iodovinyl)-3',5',6',7',8',8a'-hexahydro-2'H,5H-spiro[furan-2,1'-indolizin]-5-one 
• 119817-92-4 securinol A 
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• 111-29-5 1 ,5-pentanediol 

Downstream Products

• 1085244-06-9 (2β,15α)-14,15-dihydro-15-(4-phenylpiperazin-1-yl)securinan-11-one 
• 1085244-08-1 (2β,15α)-14,15-dihydro-15-[4-(4-methoxyphenyl)piperazin-1-yl]securinan-11-one 
• 3909-79-3 Tetrahydrosecurinin 
• 42555-40-8 1β-amino-11-oxo-securinanium; 2,4,6-trimethyl-benzenesulfonate 

Relevant articles and documents

Isolation of securinol A,B, and C from Securinega suffruticosa Rehd. and the structures of securinol A and B.

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Kinetics and mechanism of the alkaline hydrolysis of securinine

The hydroxide ion-catalyzed hydrolysis of securinine involves the ring opening of the lactone moiety. The rate of hydrolysis is insensitive to the ionic strength. The observed pseudo-first-order rate constants reveal a decrease of approximately 4-fold due to the increase in the MeCN content from 4 to 50% (v/v) in mixed aqueous solvent. The temperature dependence of the rate of hydrolysis follows the Eyring equation, which yields ΔH* and ΔS* as 11.0 kcal mol-1 and -34.5 cal deg-1 mol-1, respectively. The hydroxy carboxylate product of the alkaline hydrolysis of securinine is shown to undergo cyclization in acidic medium to yield securinine. The observed pseudo-first-order rate constants for cyclization increase linearly with an increase in [H+]. The change in the content of MeCN from 3.8 to 47.2% (v/v) in mixed aqueous solvents does not show an effect on the rate of the cyclization reaction. The most plausible mechanisms for alkaline hydrolysis and acid cyclization reactions are also discussed.

First total synthesis of (+)-viroallosecurinine

The first diastereoselective chiral synthesis of (+)-viroallosecurinine, isolated from Securinega virosa as a cytotoxic alkaloid, was achieved by using a chelation-controlled addition of an alkyne moiety to the corresponding ketone, and a ring-closing metathesis, as key reactions.

Enantioselective approach to securinega alkaloids. Total synthesis of securinine and (-)-norsecurinine

(Chemical Equation Presented) The most representative securinega alkaloids have been synthesized through a new strategy involving the palladium-catalyzed enantioselective allylation of a cyclic imide, a vinylogous Mannich reaction, and a ring-closing meta