112693-24-0

Basic information

• Product Name: 1-{2-[(7Z)-azacycloundec-7-en-2-yl]ethyl}-9H-beta-carboline
• Synonyms: Manzamine c
• CAS NO: 112693-24-0
• Molecular Formula: C₂₃H₂₉N₃
• Molecular Weight: 347.4965
• Mol File: 112693-24-0.mol

Chemical Properties

• Boiling Point: 550°C at 760 mmHg
• Flash Point: 286.4°C
• Density: 1.077g/cm³
• Vapor Pressure: 3.8E-12mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: 1-{2-[(7Z)-azacycloundec-7-en-2-yl]ethyl}-9H-beta-carboline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-{2-[(7Z)-azacycloundec-7-en-2-yl]ethyl}-9H-beta-carboline(112693-24-0)
• EPA Substance Registry System: 1-{2-[(7Z)-azacycloundec-7-en-2-yl]ethyl}-9H-beta-carboline(112693-24-0)

Safety Data

• Hazardous Substances Data: 112693-24-0(Hazardous Substances Data)

Upstream product

• 126412-12-2 (Z)-1-Aza-6-cycloundecen 
• 126440-99-1 β-carbolinemesylate 
• 126440-98-0 (Z)-1-(1-Aza-6-cycloundecen-1-yl)-2-(9H-pyrido<3,4-b>indol-1-yl)-1-ethanon 
• 486-84-0 harmane 
• 138428-34-9 1-methoxycarbonylmethyl-β-carboline 
• 138428-44-1 β-carboline potassium salt 
• 306774-43-6 (Z)-azacycloundec-6-ene-1-carboxylic acid tert-butyl ester 
• 306774-40-3 (E)-azacycloundec-6-ene-1-carboxylic acid tert-butyl ester 
• 306774-38-9 N-(t-butyloxycarbonyl)-1-thia-7-azacyclododecane 
• 306774-42-5 N-(t-butyloxycarbonyl)-6,7-cis-epoxyazacycloundecane 
• 306774-37-8 N-(t-butyloxycarbonyl)-bis(5-bromopentyl)amine 
• 306774-35-6 N-(t-butyloxycarbonyl)-bis(5-hydroxypentyl)amine 
• 306774-39-0 N-(t-butyloxycarbonyl)-2-chloro-1,1-dioxo-1-thia-7-azacyclododecane 
• 306774-36-7 methanesulfonic acid 5-[tert-butoxycarbonyl(5-methanesulfonyloxypentyl)amino]pentyl ester 

Relevant articles and documents

Manzamine C congeners with modified azacyclic rings: Synthesis and biological evaluation

Manzamine C congeners with modified azacyclic rings were synthesized using a DPPA-promoted conjunction of the β-carboline-1-acetate salt with various amines as a key reaction. A preliminary biological evaluation revealed that these analogues retained similar activities as Manzamine C.

The use of the Ramberg-Backlund rearrangement for the formation of aza-macrocycles: A total synthesis of manzamine C

A total synthesis of the marine alkaloid manzamine C has been accomplished. A Ramberg-Baklund reaction was used as a key step to construct the required azacycloundecene ring.

Synthesis of Manzamine C, Infractine and 6-Hydroxyinfractine

Manzamine C (1), a β-carboline alkaloid with antitumor activity isolated from the marine sponge Haliclona sp. was synthesized.The dilithium derivative of 5-hexynoic acid (6) was alkylated with 7 to give after esterification the methyl 10-hydroxy-5-decynoate (8).The tosylate of 8 was converted into the azide 9 which could be selectively hydrogenated with Lindlar palladium catalyst to give the amino ester 10.Saponification of 10 and acylation with (Boc)2O yielded 11, which was converted with pentafluorophenol into 12.Removal of the Boc group in 12 gave an amino ester as intermediate, which cyclized immediately under high dilution conditions to give the lactam 13 in high yield.Reduction of 13 with LiAlH4 produced the macrocyclic amine 4.The β-carboline part of 1 was prepared by condensation of N-benzyltryptamine 14 with the formylacetic acid equivalent 15 to give 16.Dehydrogenation of 16 with Pd-on-carbon catalyst led to the orthoester 17, which could be converted into the methyl ester 5 in high overall yield.The 4-(dimethylamino)pyridine-catalyzed substitution of the methyl ester function in 5 by the amine 4 gave the amide 29.The analogous reaction of 5 with pyrrolidine or with azacyclotridecane yielded 30 and 31.Reduction of these three amides with LiAlH4 produced 1, 2 and 3.The spectroscopic properties of 1 were identical with those of natural manzamine C. - Condensation of 14 or N-benzyl-5-(benzyloxy)tryptamine (19) with aldehyde 18 yielded the products 20 and 21, which could be dehydrogenated to furnish 22 and 23.From these the methyl esters 24 and 25 with properties identical to those of the known β-carboline alkaloids infractine and 6-hydroxyinfractine could be obtained.

A total synthesis of Manzamine C and its geometrical isomer

Manzamine C (1) has been synthesized from silyloxyacetylene (3) along the line: 4→5→8→18→1. The overall yield is 21%. The β-carboline segment (11) was obtained by the Bischler-Napieralski reaction of 14 followed by dehydrogenation. By the similar procedur

A total synthesis of manzamine C

Manzamine C (1) was synthesized by the conjunction of 6-(Z)-azacycloundecene (9) and 1-substituted β-carboline derivatives (10 or 13).