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Neihumicin

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Neihumicin
Category Antibiotics
Catalog number BBF-02108
CAS 111451-12-8
Molecular Weight 304.34
Molecular Formula C19H16N2O2

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Neihumicin is produced by the strain of Micromonospora neihuensis Wu, sp. nov. Neihumicin is resistant to beer saccharomyces yeast and Penicillium italium Wehmer, but not to bacteria.

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Synonyms Neihumycin; 3,6-Dibenzylidene-2-methoxy-3,6-dihydropyrazin-5-one; NSC617674; (Z,Z)-3,6-Dihydro-5-methoxy-3,6-bis(phenylmethylene)-2(1H)-pyrazinone
IUPAC Name (3Z,6Z)-3,6-dibenzylidene-5-methoxypyrazin-2-one
Canonical SMILES COC1=NC(=CC2=CC=CC=C2)C(=O)NC1=CC3=CC=CC=C3
InChI InChI=1S/C19H16N2O2/c1-23-19-17(13-15-10-6-3-7-11-15)20-18(22)16(21-19)12-14-8-4-2-5-9-14/h2-13H,1H3,(H,20,22)/b16-12-,17-13-
InChI Key CKMSPKVRKZDILM-MCOFMCJXSA-N
Appearance Yellow Crystals
Antibiotic Activity Spectrum fungi; yeast
Melting Point 175-176°C
Density 1.14 g/cm3
1. Neihumicin, a new cytotoxic antibiotic from Micromonospora neihuensis. I. The producing organism, fermentation, isolation and biological properties
R Y Wu, L M Yang, T Yokoi, K H Lee J Antibiot (Tokyo). 1988 Apr;41(4):481-7. doi: 10.7164/antibiotics.41.481.
A new cytotoxic and antifungal antibiotic, neihumicin, was isolated from the culture broth of a soil isolate identified as Micromonospora neihuensis Wu, sp. nov. Neihumicin shows in vitro cytotoxicity against KB tissue culture cells (ED50 0.94 micrograms/ml) as well as antifungal activity against Saccharomyces cerevisiae ATCC 9763.
2. Neihumicin, a new cytotoxic antibiotic from Micromonospora neihuensis. III. Structure-activity relationships
T Yokoi, L M Yang, T Yokoi, R Y Wu, K H Lee J Antibiot (Tokyo). 1988 Apr;41(4):494-501. doi: 10.7164/antibiotics.41.494.
Structure-cytotoxicity relationships studies have indicated that the C-3 and C-6 disubstituted piperazine-2,5-diones are structurally required for significant cytotoxicity, and the neihumicin-like C-3 and C-6 disubstituted unsymmetrical piperazine derivatives are, in general, more cytotoxic than the corresponding symmetrical piperazine-2,5-diones. Several synthetic analogs including 3,6-di-(2,4,5-trimethoxybenzylidene)piperazine-2,5- dione, 3,6-dibenzylidene-2-ethoxy-3,6-dihydropyrazine-5-one, 3-benzylidene-6-(m-chlorobenzylidene)-2-methoxy-3,6-dihydropyrazine++ +-5-one, have been shown to be more cytotoxic than neihumicin.
3. Neihumicin, a new cytotoxic antibiotic from Micromonospora neihuensis. II. Structural determination and total synthesis
L M Yang, R Y Wu, A T McPhail, T Yokoi, K H Lee J Antibiot (Tokyo). 1988 Apr;41(4):488-93. doi: 10.7164/antibiotics.41.488.
The structure of neihumicin, a new antibiotic isolated from the fermentation broth of Micromonospora neihuensis Wu, sp. nov., has been determined as (Z)-3,(Z)-6-dibenzylidene-2-methoxy-3,6-dihydropyrazin-5-one based upon spectral evidence and X-ray crystallographic analysis. Its total synthesis has also been achieved.

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