1150-44-3

Usage

Uses

Used in Pharmaceutical Industry:
(±)-Isochanoclavine I is used as an anti-inflammatory agent for its ability to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
(±)-Isochanoclavine I is used as an anti-microbial agent for its potential to inhibit the growth of certain microorganisms, contributing to the development of new antibiotics.
(±)-Isochanoclavine I is used as an anti-cancer agent for its significant anti-cancer properties, which may aid in the development of novel cancer treatments.
(±)-Isochanoclavine I is used as an antifungal agent for its potential to inhibit the growth of certain fungi, which could lead to the development of new antifungal medications.
Used in Neurological Applications:
(±)-Isochanoclavine I is used as a neuromodulator for its ability to modulate neurotransmitter levels in the brain, which may have potential therapeutic applications in the treatment of neurological disorders.

Upstream product

• 77784-57-7 Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester 
• 1074-86-8 4-formyl indole 
• 74447-22-6 N-[5-(1,2-Dihydroxy-ethyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-N-methyl-acetamide 
• 122866-07-3 <2aα,4β,5α(Z)>-(+/-)-3-(1-acetyl-1,2,2a,3,4,5-hexahydro-4-(methylamino)benzindol-5-yl)-2-methylprop-2-enyl acetate 
• 68156-97-8 (+/-)-6,7-seco-agroclavine 
• 65846-99-3 (Z)-(4R^*,5R^*)-5-(2 methoxycarbonyl-1propenyl)-4-(N-methylamino)-1,3,4,5-tetrahydrobenzindole 
• 106507-95-3 [(4S,5S)-5-((Z)-3-Hydroxy-2-methyl-propenyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid methyl ester 
• 76084-20-3 (E)-methyl 3-(1H-indol-4-yl)acrylate 
• 76084-22-5 (E)-3-[3-(2-Oxo-ethyl)-1H-indol-4-yl]-acrylic acid methyl ester 
• 76084-21-4 (E)-methyl-3-(3-cyanomethyl-4-indolyl)propenoate 
• 76084-15-6 ((6aR,9S,9aS)-7-Methyl-4,6,6a,7,9,9a-hexahydro-8-oxa-4,7-diaza-cyclopenta[e]acenaphthylen-9-yl)-methanol 
• 76084-14-5 methyl(6aR^*,9S^*,9aS^*)-4,6,6a,7,9,9a-hexahydro-7-methylindolo<4,3 - e,f><2,1>benzisoxazole-9-carboxylate 
• 76084-17-8 t-butyl-N-<(4R^*,5S^*,1'S^*)-5-(1',2'-dihydroxyethyl)-1,3,4,5-tetrahydrobenzindol-4-yl>N-methylcarbamate 
• 79133-62-3 (+)-4,5-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 

Downstream Products

• 95586-10-0 (+/-)-Agroclavine I 
• 548-42-5 (+/-)-Agroclavine 
• 77784-57-7 Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester 
• 77784-56-6 Acetic acid 2-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-ylmethyl]-allyl ester 
• 548-42-5 agroclavine 

Relevant academic research and scientific papers

Biomimetic Total Syntheses of Clavine Alkaloids

Biomimetic total syntheses of either enantiomers of a number of ergot alkaloids, chanoclavine I (1b), chanoclavine I aldehyde (1c), pyroclavine (1e), festuclavine (1f), pibocin A (1g), 9-deacetoxyfumigaclavine C (1h), and fumigaclavine G (1i), have been achieved from seco-agroclavine (1a). The advanced intermediate for seco-agroclavine (1a) was synthesized via a key thiourea-catalyzed intramolecular nitronate addition onto α,β-unsaturated ester.

Total Synthesis of (-)-Chanoclavine i and an Oxygen-Substituted Ergoline Derivative

An efficient and direct route to ergot alkaloid (-)-chanoclavine I (3) is described using the inexpensive compound (2R)-(+)-phenyloxirane (15) as a chiral pool in 13 steps with 17% overall yield. Key features of the synthesis include a palladium-catalyzed intramolecular aminoalkynylation of terminal olefin and a rhodium-catalyzed intramolecular [3 + 2] annulation. An oxygen-substituted ergoline derivative (-)-25 was also achieved by using the same strategy.

Synthetic studies directed toward ergot alkaloids, (±)-6,7-secoagroclavine, (±)-chanoclavine-1, (±)-chanoclavine-II, and (±)-agroclavine-I, by an efficient and common synthetic route

Novel three synthetic routes to (±)-6,7-secoagroclavine were developed from either methyl 3-(3-formylindol-4-yl)acrylate, indole-4-carbaldehyde, or 4-iodoindole-3-carbaldehyde. The total syntheses of (±)-chanoclavine-I, (±)-chanoclavine-II, and (±)-agroclavine-I were accomplished as well from the synthetic intermediates involved in the synthesis of (±)-6,7-secoagroclavine, culminating in establishing an efficient and common synthetic method for ergot alkaloids.

Simple total syntheses of (-)-ergot alkaloids and their (+)-enantiomers by a common synthesis method utilizing optical resolution

The first and simple total syntheses of (-)-isochanoclavine-1 ((-)-1b), (-)-agroclavine ((-)-3), (-)-agroclavine-1 ((-)-4), and (-)-norchanoclavine-1 ((-)-5c) and their (+)-enantiomers are achieved from indole-3-carboxaldehyde (8) by a common synthesis method utilizing optical resolution. Absolute configuration of (-)-agroclavine-1 is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-1 (1c) are also included.

Total synthesis of optically active chanoclavine-I

The total synthesis of optically active chanoclavine-I, an ergot alkaloid, was accomplished using palladium-catalyzed intramolecular cyclization (Heck-reaction) as a key step. The conjugate ester (6) was obtained in 2 steps from optically active 4-bromotryptophan (10), and the cyclization of 6 proceeded smoothly without racemization to give the key intermediate, tricyclic tetrahydrobenz[c,d]indole derivative (7), in high yield.

Photocyclisation of Enamides. Part 35. New Total Syntheses of the Ergot Alkaloids (+/-)-Chanoclavine-I and (+/-)-isochanoclavine-I using a Fragmentation of 3-Amino Alcohols

A new synthetic route involving the fragmentation reaction of 3-amino alcohols for the total synthesis of 6,7-secoergoline alkaloids was developed and then successfully applied to the total syntheses of (+/-)-chanoclavine-I and (+/-)-isochanoclavine-I.

THE FIRST TOTAL SYNTHESIS OF (+/-)-CHANOCLAVINE-I ACID AND AN ALTERNATIVE TOTAL SYNTHESIS OF (+/-)-CHANOCLAVINE-I

The total synthesis of (+/-)-chanoclavine-I acid was achieved for the first time.An alternative total synthesis of (+/-)-chanoclavine-I was also reported.

A NOVEL SYNTHESIS OF (+/-)-ISOCHANOCLAVINE-I

Total synthesis of (+/-)-isochanoclavine-I (9) was achieved via the route involving fragmentation reaction of the 3-aminoalcohol 4.

TOTAL SYNTHESES OF (+/-)-AGROCLAVINE-I, (+/-)-6-NOR-CHANOCLAVINE-II, AND (+/-)-CHANOCLAVINE-II

The first total syntheses of (+/-)-6-nor-chanoclavine-II and (+/-)-chanoclavine-II are achieved.Total synthesis of (+/-)-agroclavine-I is also reported.

SHORT-STEP SYNTHESIS OF THE ERGOT ALKALOIDS, (+/-)-NORCHANOCLAVINE-I, (+/-)-CHANOCLAVINE-I, (+/-)-ISOCHANOCLAVINE-I, and (+/-)-AGROCLAVINE

The simple total synthesis of the ergot alkaloids, (+/-)-norchanoclavine-I, (+/-)-chanoclavine-I, (+/-)-isochanoclavine-I, and (+/-)-agroclavine was achieved by a practical and common synthesis method.A new regio-selective oxidation of the Z-methyl group of the isoprenyl system with selenium dioxide is described.Keywords - (+/-)-norchanoclavine-I; (+/-)-norisochanoclavine-I; (+/-)-chanoclavine-I; (+/-)-isochanoclavine-I; (+/-)-agroclavine; ergot alkaloid; total synthesis; common synthesis method; new oxidation