215121-47-4

Basic information

• Product Name: BrevicoMpanine B
• Synonyms: BrevicoMpanine B
• CAS NO: 215121-47-4
• Molecular Formula: C22H29N3O2
• Molecular Weight: 367.48456
• Mol File: 215121-47-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BrevicoMpanine B(CAS DataBase Reference)
• NIST Chemistry Reference: BrevicoMpanine B(215121-47-4)
• EPA Substance Registry System: BrevicoMpanine B(215121-47-4)

Safety Data

• Hazardous Substances Data: 215121-47-4(Hazardous Substances Data)

Usage

Description

Brevicompanine B is a fungal metabolite originally isolated from P. brevicompactum that has plant growth and circadian rhythm regulatory activity. It inhibits hypocotyl elongation in lettuce seedlings when used at a concentration of 100 mg/L but does not inhibit elongation in rice seedlings at a concentration of 300 mg/L. Brevicompanine B (100 μM) inhibits primary root growth in Arabidopsis seedlings and disrupts the transcription of various genes involved in the regulation of plant circadian rhythm. It is active against P. falciparum with an IC50 value of 35 mg/ml.

Uses

Brevicompanine B is a diketopiperazine-related metabolite produced by Penicillium and Aspergillus species. Brevicompanine B is active against the malaria parasite, Plasmodium falciparum, and shows pronounced plant growth regulatory activity but is devoid of antifungal or antibacterial activity.

Upstream product

• 358-72-5 dimethylallyl diphosphate 
• 56941-94-7 Cyclo(L-leucyl-L-tryptophyl) 
• 861216-48-0 tert-butyl 2-methylbut-3-en-2-yl carbonate 
• 115-18-4 2-methyl-3-buten-2-ol 
• 35661-60-0 N-(9-fluorenylmethoxycarbonyl)-D-leucine 
• 338391-59-6 methyl (2S)-2-[{(2S,3aS,8aR)-1,8-bis-t-butoxycarbonyl-3a-(1,1-dimethylprop-2-enyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-2-yl}carbonylamino]-4-methylpentanoate 
• 338391-60-9 methyl (2S)-2-[{(2S,3aS,8aR)-3a-(1,1-dimethylprop-2-enyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-2-yl}carbonylamino]-4-methylpentanoate 
• 159333-19-4 (2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1,8-di-tert-butyl ester 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 338391-57-4 methyl (2R)-2-[{(2S,3aS,8aR)-1,8-bis-t-butoxycarbonyl-3a-(1,1-dimethylprop-2-enyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-2-yl}carbonylamino]-4-methylpentanoate 
• 338391-58-5 methyl (2R)-2-[{(2S,3aS,8aR)-3a-(1,1-dimethylprop-2-enyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-2-yl}carbonylamino]-4-methylpentanoate 
• 5845-53-4 (R)-leucine methyl ester hydrochloride 

Relevant articles and documents

Ir-catalyzed reverse prenylation of 3-substituted indoles: Total synthesis of (+)-aszonalenin and (-)-brevicompanine B

The selective reverse prenylation of 3-substituted-1H-indoles at C3 is described. The iridium-catalyzed reaction proceeds with high branched to linear selectivity (>20:1) for a variety of indoles. In addition, a diastereoselective reverse prenylation of tryptophan methyl ester is disclosed, and its synthetic utility is demonstrated in the synthesis of (+)-aszonalenin and (-)-brevicompanine B.

Synthesis of brevicompanines, plant growth regulators

Brevicompanine A (1) and B (2) are plant growth regulators isolated from Penicillium brevicompactum. The synthesis of brevicompanine A (1) and B (2) was accomplished via a known intermediate.