2650-35-3

Basic information

• Product Name: norsecurinine
• Synonyms: norsecurinine;(-)-6-Norsecurinan-11-one;(6S,10aR,10bS)-8,9,10,10a-Tetrahydro-6,10b-Methano-10bH-furo[2,3-c]pyrrolo[1,2-a]azepin-2(6H)-one;[6S-(6α,10aβ,10bα)]-8, 9,10,10a-Tetrahydro-6,10b-Methano-10bH-furo[2,3-c]pyrrolo[1,2-a]azepin-2(6H)-one;A-Norsecurinan-11-one
• CAS NO: 2650-35-3
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.23712
• Product Categories: Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 2650-35-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 453.8°C at 760 mmHg
• Flash Point: 200.9°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 2E-08mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: norsecurinine(CAS DataBase Reference)
• NIST Chemistry Reference: norsecurinine(2650-35-3)
• EPA Substance Registry System: norsecurinine(2650-35-3)

Safety Data

• Hazardous Substances Data: 2650-35-3(Hazardous Substances Data)

Usage

Description

Norsecurinine is an alkaloid derived from the plant Phyllanthus niruri, which is known for its medicinal properties. It possesses various bioactive compounds that contribute to its potential therapeutic applications.

Uses

Used in Pharmaceutical Applications:
Norsecurinine is used as a therapeutic agent for various diseases, including poliomyelitis, ALS (amyotrophic lateral sclerosis), and chronic aplastic anemia. Its bioactive properties make it a promising candidate for clinical use in treating these conditions.
Used in Traditional Medicine:
Norsecurinine is also used in traditional medicine, particularly in the treatment of various ailments due to its alkaloid nature and the medicinal properties of the Phyllanthus niruri plant.

InChI:InChI=1/C12H13NO2/c14-11-6-8-3-4-9-7-12(8,15-11)10-2-1-5-13(9)10/h3-4,6,9-10H,1-2,5,7H2/t9-,10-,12?/m1/s1

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Relevant articles and documents

Stereoselective total syntheses of (-)-flueggine A and (+)-virosaine B

Convergent approach: The total syntheses of (-)-flueggine A and (+)-virosaine B (see scheme) have been accomplished in a concise and convergent manner. Key steps in these approaches were relay ring-closing metathesis reactions for rapid construction of the key intermediates, and 1,3-dipolar cycloaddition reactions for the formation of the natural products. Copyright

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

Total syntheses of the Securinega alkaloids (+)-14,15-dihydronorsecurinine, (-)-norsecurinine, and phyllanthine

A new strategy for enantiospecific construction of the Securinega alkaloids has been developed and applied in total syntheses of (+)-14,15-dihydronorsecurinine (8), (-)-norsecurinine (6), and phyllanthine (2). The B-ring and C7 absolute stereochemistry of these biologically active alkaloids originated from trans-4-hydroxy-L-proline (10), which was converted to ketonitrile 13 via a high-yielding eight-step sequence. Treatment of this ketonitrile with SmI2 afforded the 6-azabicyclo-[3.2.1]octane B/C-ring system 14, which is a key advanced intermediate for all three synthetic targets. Annulation of the A-ring of (-)-norsecurinine (6) with the required C2 configuration via an N-acyliminium ion alkylation was accomplished using radical-based amide oxidation methodology developed in these laboratories as a key step, providing tricycle 33. Annulation of the D-ring onto α-hydroxyketone 33 with the Bestmann ylide 45 at 12 kbar gave (+)-14,15-dihydronorsecurinine (8). In the securinine series, the D-ring was incorporated using an intramolecular Wadsworth-Horner-Emmons olefination of phenylselenylated α-hydroxyketone 47. The C14,15 unsaturation was installed late in the synthesis by an oxidative elimination of the selenoxide derived from tetracyclic butenolide 50 to give (-)-norsecurinine (6). The A-ring of phyllanthine (2) was formed from hydroxyketone 14 using a stereoselective Yb(OTf)3-promoted hetero Diels-Alder reaction of the derived imine 34 with Danishefsky's diene, affording adduct 35. Conjugate reduction and stereoselective equatorial ketone reduction of vinylogous amide 35 provided tricyclicintermediate 36, which could then be elaborated in a few steps to stable hydroxyenone 53 via α-selenophenylenone intermediate 52. The D-ring was then constructed, again using an intramolecular Wadsworth-Horner-Emmons olefination reaction to give phyllanthine (2).