[(6R,7S,8R)-11-Amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

Base Information

• Chemical Name: [(6R,7S,8R)-11-Amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
• CAS No.: 50-07-7
• Molecular Formula: C15H18N4O5
• Molecular Weight: 334.332
• Hs Code.: 29419090
• NSC Number: 755880
• Wikidata: Q27163543
• Mol file: 50-07-7.mol

Synonyms:[(6R,7S,8R)-11-Amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate;SR-05000001845;Spectrum2_000920;Spectrum3_001792;Spectrum4_000929;Spectrum5_001888;BSPBio_003343;KBioGR_001458;SPECTRUM330002;DivK1c_001034;SPBio_000800;CHEBI:91730;HMS503O09;KBio1_001034;KBio3_002845;NINDS_001034;HMS1923I11;HMS2091C19;Pharmakon1600-00330002;LSM-1590;CCG-39750;NSC755880;NSC-755880;IDI1_001034;NCGC00178129-01;AB00051901_02;SR-05000001845-1;SR-05000001845-4;SR-05000001845-5;BRD-A48237631-001-02-2;BRD-A48237631-001-03-0;Q27163543

Chemical Property of [(6R,7S,8R)-11-Amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

Chemical Property:

• Appearance/Colour: dark blue grey crystalline powder
• Vapor Pressure: 1.59E-13mmHg at 25°C
• Melting Point: 360 °C
• Refractive Index: 1.68
• Boiling Point: 581.78 °C at 760 mmHg
• PKA: pKa 2.8(H2O,t =25,I=0.1) (Uncertain)
• Flash Point: 305.65 °C
• PSA: 146.89000
• Density: 1.564 g/cm³
• LogP: 0.01610
• Storage Temp.: 2-8°C
• Solubility.: H2O: 4 mL/vial Stock solutions should be filter sterilized
• Water Solubility.: soluble
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 334.12771969
• Heavy Atom Count: 24
• Complexity: 757

Purity/Quality:

99%min ^*data from raw suppliers

Mitomycin C ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn,T+
• Hazard Codes: T,Xn,T+
• Statements: 25-40-22-45-26/27/28
• Safety Statements: 36/37-45-28A-28-53-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=O)C2=C(C1=O)N3CC4C(C3(C2COC(=O)N)OC)N4)N
• Isomeric SMILES: CC1=C(C(=O)C2=C(C1=O)N3CC4[C@H]([C@]3([C@H]2COC(=O)N)OC)N4)N
• description: Mitomycin C (MMC), an antineoplastic antibiotic derived from Streptomyces caespitosus or Streptomyces lavendulae, is a cell cycle-specific alkylating agent, inhibits DNA synthesis through covalent mitomycin C-DNA adduct with EC50 values of 0.14μM in PC3 cells. Therefore, it was served as a chemotherapeutic agent that has demonstrated its antitumor activity and has been used widely in treatment of various cancers. Although it is active against a wide variety of tumors, newer agents have largely replaced MMC except in anal cancer; outside of the United States, MMC is infrequently used for treatment of advanced non-small cell lung cancer (NSCLC), and breast cancer.
• Uses: (1) It is a cell division inhibitors, nucleic acid inhibitors and phage inducer; an anti-tumor drugs in clinical use. (2) This drug has a broad anti-tumor spectrum, and effective for gastric cancer, breast cancer. It has a certain effect on lung cancer, liver cancer, malignant lymphoma, Hodgkin's disease, reticular cell sarcoma, uterine cancer, leukemia, intestinal cancer and pancreatic cancer, but with a short remission. Combination with urokinase can improve the efficacy. The goods exert its function quickly, but the number of operators is not high, and it has a high toxicity. The goods and bleomycin as well as its derivatives ——doxorubicin are anti-cancer drugs of antibiotic which can disrupt DNA. It can depolymerize DNA in the cell, inhibit DNA replication in proliferating cell. The LD50 of intravenous injection of mice is 5ml/kg. It acts as an anticancer drugs, commonly used in the treatment of digestive system cancers. Mitomycin C USP (Mutamycin) is used to treat chronic myelogenous leukemia; reticulum cell sarcoma; Hodgkin.s disease; non-Hodgkin.s lymphomas; cancer of stomach, pancreas, lung; epithelial tumors. Mitomycin C is the most studied of a family of highly distinctive blue/purple metabolites produced by several Streptomyces species. Mitomyin C exhibits potent antibacterial and antitumour activity and inhibits DNA synthesis by intercalation, blocking nuclear division with the induction of apoptosis in cancer cells.
• Description: Mitomycin C is naturally produced by Streptomyces caespitosus, an Actinobacteria found in soil. Mitomycin C has antibiotic and antitumor activities and has been studied extensively since the 1950s. A unique feature of this drug is strong bioreductive alkylation under hypoxic conditions. Oxygen-poor cells internal to solid tumors provide an environment in which this drug is highly activated. As an antitumor agent, it has shown efficacy in a wide variety of cancers, including gastric cancer, pancreatic cancer, breast cancer, non-small-cell lung cancer, cervical cancer, prostate cancer, and bladder cancer. The sideeffect profile is large, which prohibits its widespread use. Mitomycin C is antibacterial to gram-positive, gram-negative, and acid-fast bacilli.
• Indications: Mitomycin (mitomycin C, Mitocin-C, Mutamycin) is an antibiotic that is derived from a species of Streptomyces. It is sometimes classified as an alkylating agent because it can covalently bind to and cross-link DNA. Mitomycin is thought to inhibit DNA synthesis through its ability to alkylate double-strand DNA and bring about interstrand cross-linking. There is evidence that enzymatic reduction by a reduced nicotinamide– adenine dinucleotide phosphate (NADPH) dependent reductase is necessary to activate the drug. The drug is rapidly cleared from serum after intravenous injection but is not distributed to the brain.
• Therapeutic Function: Cancer chemotherapy
• Clinical Use: Mitomycin has limited palliative effects in carcinomas of the stomach, pancreas, colon, breast, and cervix.
• Drug interactions: Potentially hazardous interactions with other drugs Antipsychotics: avoid with clozapine (increased risk of agranulocytosis). Live vaccines: risk of generalised infections - avoid.

Technology Process of [(6R,7S,8R)-11-Amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

There total 25 articles about [(6R,7S,8R)-11-Amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate 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: 99.0%

albomitomycin A (110934-24-2) → mitomycin C (50-07-7)

Guidance literature:

With ammonia; at 25 ℃; for 0.5h;

DOI:10.1021/jo00052a052

Reference yield: 92.0%

2-((2-(piperidin-1-yl)ethyl)disulfanyl)ethyl(1aS,8S,8aR,8bS)-6-amino-8-((carbamoyloxy)methyl)-8a-methoxy-5-methyl-4,7-dioxo-1a,4,7,8,8a,8b-hexahydroazirino [2’,3’:3,4]pyrrolo[1,2-a]indole-1(2H)-carboxylate → mitomycin C (50-07-7)

Guidance literature:

With l-cysteine hydrochloride; In ethanol; water; at 37 ℃; for 2h;

Reference yield: 85.0%

→ mitomycin C (50-07-7)

Guidance literature:

upstream raw materials:

1a-acetyl-7-demethoxy-6,7-dihydro-7,7-(ethylenedioxy)-6-(phenylselenyl)mitomycin A

2-(2-Pyridinyldithio)benzylmitomycin C-1a-carboxylate

7-<<(dimethylamino)methylene>amino>-9a-methoxymitosane

isomitomycin A

Downstream raw materials:

7-amino-9a-methoxy-1a-<(phenylthio)thiocarbonyl>mitosane

1a-Acetylmitomycin C

C₂₂H₂₃N₃O₆

C₂₂H₂₄N₄O₅

Refernces

• 1、 Chen,Coppola,Johns,Bogardus,Lipper. "Degradation kinetics and mechanism of N6-[(dimethylamino)methylene]mitomycin C in aqueous solutions". . p. 208 - 210. Retrieved 1986.
• 2、 Sun, Tao,Morger, Andrea,Castagner, Bastien,Leroux, Jean-Christophe. "An oral redox-sensitive self-immolating prodrug strategy". supporting information. p. 5721 - 5724. Retrieved 2015/03/30.
• 3、 -. "Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same". . . Retrieved 2010/05/13.