13164-90-4

Usage

Uses

Used in Pharmaceutical Industry:
(1aS)-1,5-Dimethyl-6-methoxy-8β-(carbamoyloxymethyl)-8aα-hydroxy-1,1aα,2,8,8a,8bα-hexahydroazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione is used as an intermediate in the synthesis of mitomycin B (M371895), an antitumor antibiotic with antineoplastic properties. Mitomycin B is utilized in the treatment of various types of cancer, including gastric, pancreatic, colorectal, and lung cancers, due to its ability to cross-link DNA strands and inhibit DNA replication and transcription.
Used in Chemical Research:
As a complex organic molecule with a unique structure, (1aS)-1,5-Dimethyl-6-methoxy-8β-(carbamoyloxymethyl)-8aα-hydroxy-1,1aα,2,8,8a,8bα-hexahydroazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione may also be used in chemical research for the development of new synthetic routes, the study of reaction mechanisms, and the exploration of novel chemical properties. Its potential applications in the synthesis of other bioactive compounds or the development of new pharmaceutical agents could be of interest to researchers in the field.

Upstream product

• 186581-53-3 diazomethane 
• 79026-43-0 9-epi-mitomycin D 
• 78879-23-9 C₁₄H₁₇N₃O₄ 
• 105551-82-4 9-epi-10-O-decarbamoyl-10-O-<(trichloroacetyl)carbamoyl>mitomycin D 
• 78879-24-0 9-epi-10-O-decarbamoyl-10-O-(phenoxycarbonyl)mitomycin D 
• 18209-14-8 N-methylmitomycin A 
• 102831-59-4 leucomitomycin 

Downstream Products

• 18209-14-8 N-methylmitomycin A 

Relevant academic research and scientific papers

On the Remarkable Stability of Derivatives of Leucomitomycin F. Novel Mitomycin Analogues

The leuco form of mitomycin F reacts with silica gel in the presence of oxygen to afford 9-epimitomycin B.A notable stability is manifested by hydroquinoid forms (leucomitomycin) bearing a 9,10-exocyclic methylene group.

Synthesis of 9-epi-Mitomycin B: The First Inversion of the C-9 Stereochemistry in Mitomycin B

9-epi-Mitomycin B (2b) with the same C-9 stereochemistry as mitomycin C(1) was synthesized from mitomycin B (2a) through inversion at the C-9 position. 10-O-Decarbamoylmitomycin D (8a), derived from 2a in two steps, was employed as the substrate for the epimerization.The 10-hydroxymethyl group in 8a was epimerized on treatment with diazabicycloundec-7-ene to afford 8b.Successive transformation performed on the functional groups of 8b gave the desired 2b in four steps.The stereochemistry in 2b was confirmed by conversion of 2b to the known mitomycin F (4).