18210-71-4

Basic information

• Product Name: hodgkinsine
• Synonyms: hodgkinsine;(3aS,3'aR,3''aR,8aS,8'aR,8''aS)-2,2',2'',3,3',3'',8,8',8'',8a,8'a,8''a-Dodecahydro-1,1',1''-trimethyl-3a,3'a(1H,1'H):7',3''a(1''H)-ter(pyrrolo[2,3-b]indole)
• CAS NO: 18210-71-4
• Molecular Formula: C₃₃H₃₈N₆
• Molecular Weight: 518.71
• Mol File: 18210-71-4.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.258g/cm³
• Refractive Index: 1.67
• CAS DataBase Reference: hodgkinsine(CAS DataBase Reference)
• NIST Chemistry Reference: hodgkinsine(18210-71-4)
• EPA Substance Registry System: hodgkinsine(18210-71-4)

Safety Data

• Hazardous Substances Data: 18210-71-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Hodgkinsine is used as an antimalarial agent for its significant antiplasmodial activity, offering a promising alternative for the development of new antimalarial drugs.
Used in Pain Management Applications:
Hodgkinsine is employed as an analgesic agent due to its demonstrated potential in preclinical studies to alleviate pain.
Used in Anti-Inflammatory Applications:
Hodgkinsine is utilized as an anti-inflammatory agent, showing potential to reduce inflammation in various conditions based on its preclinical properties.

InChI:InChI=1/C33H38N6/c1-37-18-15-31(21-9-4-6-13-25(21)34-28(31)37)23-11-8-12-24-27(23)36-30-33(24,17-20-39(30)3)32-16-19-38(2)29(32)35-26-14-7-5-10-22(26)32/h4-14,28-30,34-36H,15-20H2,1-3H3/t28-,29+,30-,31-,32-,33+/m1/s1

Upstream product

• 454450-82-9 meso-di-tert-butyl 1,1′-dimethyl-1,1′,2,2′,3,3a,3′,3′a-octahydro-3a,3′abipyrrolo[2,3-b]indole-8,8′(8aH,8a′H)-dicarboxylate 
• 4147-37-9 meso-Chimonanthine 

Downstream Products

• 112262-96-1 (-)-calycosidine 
• 112262-96-1 (-)-calycosidine 

Relevant articles and documents

Enantioselective total syntheses of the cyclotryptamine alkaloids hodgkinsine and hodgkinsine B

A late-stage resolution of the meso-3a, 3a′-bispyrrolidinoindoline unit of rac-7 in a catalytic asymmetric transformation ear-marks the remarkably short, ten-step, total syntheses of hodgkinsine and hodgkinsine B. The enantioselective total synthesis of hodgkinsine B establishes the relative and absolute configuration of this trispyrrolidinoindoline alkaloid.

Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines

The enantioselective total synthesis of (-)-hodgkinsine, (-)-calycosidine, (-)-hodgkinsine B, (-)-quadrigemine C, and (-)-psycholeine through a diazene-directed assembly of cyclotryptamine fragments is described. Our synthetic strategy enables multiple and directed assembly of intact cyclotryptamine subunits for convergent synthesis of highly complex bis- and tris-diazene intermediates. Photoextrusion of dinitrogen from these intermediates enables completely stereoselective formation of all C3a-C3a′ and C3a-C7′ carbon-carbon bonds and all the associated quaternary stereogenic centers. In a representative example, photoextrusion of three dinitrogen molecules from an advanced intermediate in a single-step led to completely controlled introduction of four quaternary stereogenic centers and guided the assembly of four cyclotryptamine monomers en route to (-)-quadrigemine C. The synthesis of these complex diazenes was made possible through a new methodology for synthesis of aryl-alkyl diazenes using electronically attenuated hydrazine-nucleophiles for a silver-promoted addition to C3a-bromocyclotryptamines. The application of Rh- and Ir-catalyzed C-H amination reactions in complex settings were used to gain rapid access to C3a- and C7-functionalized cyclotryptamine monomers, respectively, used for diazene synthesis. This convergent and modular assembly of intact cyclotryptamines offers the first solution to access these alkaloids through completely stereoselective union of monomers at challenging linkages and the associated quaternary stereocenters as illustrated in our synthesis of five members of the oligocyclotryptamine family of alkaloids.

DIAZENE DIRECTED MODULAR SYNTHESIS OF COMPOUNDS WITH QUATERNARY CARBON CENTERS

Diazene-directed modular synthesis is described for the preparation Csp2-Csp3 and Csp3-Csp3 linkages where one or more stereogenic quaternary carbon centers are formed. The disclosed methods are directed to the preparation of compounds of Formula (I), or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, from compounds of Formula (II): wherein R1-R5 and q are as defined independently for each occurrence herein. A wide variety of compounds can be accessed in this manner, including oligocyclotryptamines, where the stereochemistry of each subunit is beneficially secured before fragment coupling.

DIAZENE DIRECTED MODULAR SYNTHESIS OF COMPOUNDS WITH QUATERNARY CARBON CENTERS

Diazene-directed modular synthesis is described for the preparation Csp2-Csp3 and Csp3-Csp3 linkages where one or more stereogenic quaternary carbon centers are formed. The disclosed methods are directed to the preparation of compounds of Formula (I), or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, from compounds of Formula (II) wherein R1-R5 and q are as defined independently for each occurrence herein. A wide variety of compounds can be accessed in this manner, including oligocyclotryptamines, where the stereochemistry of each subunit is beneficially secured before fragment coupling.