paraherquamide

Base Information

• Chemical Name: paraherquamide
• CAS No.: 77392-58-6
• Molecular Formula: C28H35 N3 O5
• Molecular Weight: 493.603
• Mol file: 77392-58-6.mol

Synonyms:Paraherquamide;(-)-Paraherquamide; (-)-Paraherquamide A; Paraherquamide A;Spiro[4H,8H-[1,4]dioxepino[2,3-g]indole-8,7'(8'H)-[5H,6H-5a,9a](iminomethano)[1H]cyclopent[f]indolizine]-9,10'(10H)-dione,2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-, [1'R-(1'a,5'ab,7'b,8'ab,9'ab)]-; VM 29919; [1'R-(1'a,5'ab,7'b,8'ab,9'ab)]-2',3',8'a,9'-Tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethylspiro[4H,8H-[1,4]dioxepino[2,3-g]indole-8,7'(8'H)-[5H,6H-5a,9a](iminomethano)[1H]cyclopent[f]indolizine]-9,10'(10H)-dione

Chemical Property of paraherquamide

Chemical Property:

• Melting Point: 244-247° (dec)
• PSA: 91.34000
• LogP: 2.80990

Purity/Quality:

98% ^*data from raw suppliers

ParaherquamideA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Paraherquamide A is a mycotoxin anthelmintic originally isolated from P. paraherquei. It binds to acetylcholine receptors (IC50 = 0.5 nM for head homogenates of M. domestica) and acts as an antagonist. Paraherquamide A is toxic to C. elegans (LD50 = 2.5 μg/ml) and effective against T. colubriformis infection in gerbils when used at doses ranging from 0.39 to 200 mg/kg. It is toxic to mice (LD50 = 14.9 mg/kg).
• Uses: Paraherquamide A was first reported as a mycotoxin related to the indole tremorgenic mycotoxins. Subsequent research identified a potent, non-toxic paralysis of nematodes which led to the metabolite's development as a candidate anthelmintic. Paraherquamide A is a selective, competitive, cholinergic antagonist that distinguishes subtypes of cholinergic receptors. Paraherquamide A is a selective, competitive, cholinergic antagonist.

Technology Process of paraherquamide

There total 58 articles about paraherquamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 42.0%

methylmagnesium bromide (75-16-1) + (5aS,7'R,8'aS,9aR)-2',3',8'a,9'-tetrahydro-4,4,8',8',11'-pentamethyl-spiro[4H,8H-[1,4]dioxepino[2,3-g]indole-8,7'(8'H)-[5H,6H-5a,9a](iminomethano)[1H]-cyclopent[f]indolizine]-1',9,10'(10H)-trione (125439-06-7) → Paraherquamide (77392-58-6)

Guidance literature:

In tetrahydrofuran;

DOI:10.1002/1521-3773(20000717)39:14<2540::AID-ANIE2540>3.0.CO;2-R

Reference yield:

(5aS,7'R,8'aS,9aR)-2,2',3,3',8'a,9'-hexahydro-3-hydroxy-4,4,8',8',11'-pentamethyl-spiro[4H,8H-[1,4]dioxepino[2,3-g]indole-8,7'(8'H)-[5H,6H-5a,9a](iminomethano)[1H]cyclopent[f]indolizine]-1',9,10'(10H)-trione (296228-96-1) → Paraherquamide (77392-58-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / methyl triphenoxyphosphonium iodide; DMPU / 21 h / 20 °C

2: 42 percent / tetrahydrofuran; diethyl ether / 1 h / -30 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; methyltriphenoxyphosphonium iodide; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja036713+

Reference yield:

C27H32ClN3O5 → Paraherquamide (77392-58-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 5.5 mg / aq. TsOH / tetrahydrofuran / 0.5 h / Heating

2: 57 percent / methyl triphenoxyphosphonium iodide; DMPU / 21 h / 20 °C

3: 42 percent / tetrahydrofuran; diethyl ether / 1 h / -30 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; methyltriphenoxyphosphonium iodide; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja036713+

upstream raw materials:

5-Bromoparaherquamide

14-Oxo-5-bromo-17-norparaherquamide

methylmagnesium bromide

(5aS,7'R,8'aS,9aR)-2',3',8'a,9'-tetrahydro-4,4,8',8',11'-pentamethyl-spiro[4H,8H-[1,4]dioxepino[2,3-g]indole-8,7'(8'H)-[5H,6H-5a,9a](iminomethano)[1H]-cyclopent[f]indolizine]-1',9,10'(10H)-trione

Downstream raw materials:

Derquantel

C₃₄H₃₈BrN₃O₅

C₃₄H₃₉N₃O₅

Refernces

• 1、 Williams, Robert M.,Cao, Jianhua,Tsujishima, Hidekazu,Cox, Rhona J.. "Asymmetric, stereocontrolled total synthesis of paraherquamide A". . p. 12172 - 12178. Retrieved 2007/10/03.
• 2、 Blizzard, Timothy A.,Mrozik, Helmut,Fisher, Michael H.,Schaeffer, James M.. "Chemical Modification of Paraherquamide. 2. Replacement of the C-14 Methyl Group". . p. 2256 - 2259. Retrieved 2007/10/02.