18209-14-8

Usage

Uses

Used in Pharmaceutical Industry:
N-methylmitomycin A is used as an intermediate in the synthesis of mitomycin B (M371895), an antitumor antibiotic with significant antineoplastic activity. This makes it a valuable component in the development of cancer therapeutics, potentially offering new avenues for the treatment of various malignancies.
As an antineoplastic agent, N-methylmitomycin A may contribute to the inhibition of tumor growth and the disruption of cancer cell metabolism, thereby playing a crucial role in cancer treatment and management. Its specific application in the pharmaceutical industry could involve its use in the formulation of drugs targeting a range of cancer types, leveraging its unique structural features to enhance therapeutic efficacy and selectivity.

InChI:InChI=1/C17H21N3O6/c1-7-12(21)11-10(13(22)14(7)24-3)8(6-26-16(18)23)17(25-4)15-9(19(15)2)5-20(11)17/h8-9,15H,5-6H2,1-4H3,(H2,18,23)/t8-,9+,15+,17-,19?/m1/s1

Upstream product

• 105551-82-4 9-epi-10-O-decarbamoyl-10-O-<(trichloroacetyl)carbamoyl>mitomycin D 
• 801-52-5 porfiromycin 
• 50-07-7 mitomycin C 
• 186581-53-3 diazomethane 
• 10104-18-4 C₁₆H₁₉N₃O₆ 
• 79026-43-0 9-epi-mitomycin D 
• 78879-23-9 C₁₄H₁₇N₃O₄ 
• 4055-39-4 mitomycin A 
• 74-88-4 methyl iodide 
• 13164-90-4 9-epimitomycin B 
• 77-78-1 dimethyl sulfate 
• 102831-59-4 leucomitomycin 
• 78879-24-0 9-epi-10-O-decarbamoyl-10-O-(phenoxycarbonyl)mitomycin D 

Downstream Products

• 78142-96-8 C₂₂H₂₄N₄O₆ 
• 13164-90-4 9-epimitomycin B 
• 15973-07-6 7-methoxy-1,2-(N-methylaziridino)mitosene 
• 364753-67-3 C₂₂H₃₀N₄O₆ 
• 364753-66-2 C₂₂H₃₀N₄O₆ 
• 801-52-5 porfiromycin 

Relevant academic research and scientific papers

Convergent synthesis of a steroidal antiestrogen-mitomycin C hybrid using "click" chemistry

A convergent synthesis of a novel estrogen receptor-targeted drug hybrid was developed based on structures of the potent anti-proliferative mitomycin C and the steroidal anti-estrogen RU 39411. The steroidal antiestrogen was prepared with an azido-triethylene glycoloxy linker while the mitomycin C derivative (porfirimycin) incorporated a complementary 7-N-terminal alkyne. The two components were ligated using the Huisgen [3 + 2] cycloaddition ("click") reaction. Preliminary biological assays demonstrated that the final hybrid compound retained both potent anti-estrogenic and anti-proliferative activities.

STEROIDAL ANTI-HORMONE HYBRIDS

Disclosed are novel compounds and compositions for inhibition of androgen and estrogen receptor signaling, methods for inhibiting androgen signaling, methods for inhibiting estrogen signaling, methods for inhibiting the interaction between a co-regulatory protein and an androgen or estrogen receptor, and methods for treating cancer.

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).

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.