5,21-Dichloro-3-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione

Base Information

• Chemical Name: 5,21-Dichloro-3-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
• CAS No.: 93908-02-2
• Molecular Formula: C₂₇H₂₁Cl₂N₃O₇
• Molecular Weight: 570.386
• NSC Number: 359079
• Wikidata: Q104195734
• ChEMBL ID: CHEMBL27000
• Mol file: 93908-02-2.mol

Synonyms:MLS002701854;5,21-Dichloro-3-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione;C27H21Cl2N3O7;C27-H21-Cl2-N3-O7;NSC359079;NSC-359079;Neuro_000196;CHEMBL27000;SCHEMBL12961242;ICX5609244;NCI60_003256;SMR001565446;A20190;UNII-Y96MQM21V9;CHEMBL370100;Y96MQM21V9;5H-Indolo[2,4-c]carbasole-5,7(6H)-dione, 1,11-dichloro-12,13-dihydro-12-(4-O-methyl-.beta.-D-glucopyranosyl)-;5H-Indolo[2,4-c]carbazole-5,7(6H)-dione, 1,11-dichloro-12,13-dihydro-12-(4-O-methyl-.beta.-D-glucopyranosyl)-

Chemical Property of 5,21-Dichloro-3-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 150.37000
• Density: 1.87g/cm³
• LogP: -1.27480
• Storage Temp.: −20°C
• Solubility.: DMSO: ≥3 mg/mL
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 569.0756554
• Heavy Atom Count: 39
• Complexity: 1010

Purity/Quality:

99% ^*data from raw suppliers

Rebeccamycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1C(OC(C(C1O)O)N2C3=C(C=CC=C3Cl)C4=C5C(=C6C7=C(C(=CC=C7)Cl)NC6=C42)C(=O)NC5=O)CO
• Uses: Rebeccamycin is an indolocarbazole isolated from Lechevalieria aerocolonigenes. Rebeccamycin displays selective antitumour activity against several cell lines. Rebeccamycin's primary mechanism of action is via strong DNA intercalation resulting in the potent catalytic inhibition of both topoisomerases I and II. Analogues of rebecamycin have beend tested in clinical trials for cancer therapy. Rebeccamycin is a novel indolocarbazole topoisomerase I inhibitor.

Technology Process of 5,21-Dichloro-3-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione

There total 5 articles about 5,21-Dichloro-3-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione 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: 83.0%

1,11-dichloro-12,13-dihydro-12-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-5H-indolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7(6H)-dione → rebeccamycin (93908-02-2)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; for 2h;

DOI:10.1021/jo982277b

Reference yield:

6-(benzyloxymethyl)-1,11-dichloro-12-(3,6-di-O-benzyl-4-O-methyl-β-glucopyranosyl)indolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7-dione → rebeccamycin (93908-02-2)

Guidance literature:

With ammonia; hydrogen; palladium dihydroxide; Yield given. Multistep reaction; 1) EtOH, ethyl acetate, 5 h, 2) THF, r.t., 2 h;

DOI:10.1021/jo00054a015

Reference yield:

1-bromo-2,3,6-tri-O-acetyl-4-O-methylglucose (502498-34-2) → rebeccamycin (93908-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / Ag₂O / benzene / Heating

2: 1.) H₂, Pd/C, 2.) NH₃ / 1.) hydrogenation, 2.) ammonolysis

With palladium on activated charcoal; ammonia; hydrogen; silver(l) oxide; In benzene;

DOI:10.1016/S0040-4039(00)89281-3

upstream raw materials:

C₄₁H₃₅Cl₂N₃O₁₁

1-bromo-2,3,6-tri-O-acetyl-4-O-methylglucose

1,11-dichloro-12,13-dihydro-6-[(phenylmethoxy)methyl]-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione

Downstream raw materials:

1,11-dichloro-12[4-O-methyl-β-D-(2'-O-tosyl)glucopyranosyl]-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]-pyrrolo[3,4-c]-carbazole-5,7-dione

Refernces

• 1、 Gallant, Michel,Link, James T.,Danishefsky, Samuel J.. "A Stereoselective Synthesis of Indole-β-N-glycosides: An Application to the Synthesis of Rebeccamycin". . p. 343 - 349. Retrieved 2007/10/02.