Name: Seco-Duocarmycin MA
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Carbamic acid, N-[4-[[[2-[[(1S)-1-(chloromethyl)-1,2-dihydro-5-hydroxy-3H-benz[e]indol-3-yl]carbonyl]-1H-indol-6-yl]amino]carbonyl]phenyl]-, 1,1-dimethylethyl ester;

IUPAC Name

tert-butyl N-[4-[[2-[(1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-6-yl]carbamoyl]phenyl]carbamate

Canonical SMILES

CC(C)(C)OC(=O)NC1=CC=C(C=C1)C(=O)NC2=CC3=C(C=C2)C=C(N3)C(=O)N4CC(C5=C4C=C(C6=CC=CC=C65)O)CCl

InChI

InChI=1S/C34H31ClN4O5/c1-34(2,3)44-33(43)37-22-11-8-19(9-12-22)31(41)36-23-13-10-20-14-27(38-26(20)15-23)32(42)39-18-21(17-35)30-25-7-5-4-6-24(25)29(40)16-28(30)39/h4-16,21,38,40H,17-18H2,1-3H3,(H,36,41)(H,37,43)/t21-/m1/s1

InChIKey

MZXQBIDDBQCHFP-OAQYLSRUSA-N

Appearance

Soild powder

Shipping

Room temperature, or blue ice upon request.

1. Structural necessity of indole C5-O-substitution of seco-duocarmycin analogs for their cytotoxic activity

Eunsook Ma, Taeyoung Choi Molecules . 2010 Nov 8;15(11):7971-84. doi: 10.3390/molecules15117971.

A series of racemic indole C5-O-substituted seco-cyclopropylindole (seco-CI) compounds 1-5 were prepared by coupling in the presence of EDCI of 1-(tert-butyloxycarbonyl)-3-(chloromethyl)indoline (seg-A) with 5-hydroxy-, 5-O-methylsulfonyl, 5-O-aminosulfonyl, 5-O-(N,N-dimethylaminosulfonyl)- and 5-O-benzyl-1H-indole-2-carboxylic acid as seg-B. Compounds 1-5 were tested for cytotoxic activity against four human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using a MTT assay. Compounds 2 and 3 with small sized sulfonyl substituents like 5-O-methylsulfonyl and 5-O-aminosulfonyl exhibit a similar level of activity as doxorubicin against all cell lines tested.

2. Structural influence of indole C5-N-substitutents on the cytotoxicity of seco-duocarmycin analogs

Eunsook Ma, Taeyoung Choi Arch Pharm Res . 2011 Mar;34(3):357-67. doi: 10.1007/s12272-011-0302-1.

A series of racemic indole C5-substituted seco-cyclopropylindoline compounds (2,3 and 5-7) were prepared by coupling 1-(tert-butyloxycarbonyl)-3-(chlorocarbonyl)indoline (seg-A) with 5,6,7-trimethoxy-, 5,6-dimethoxy-, 5-amino-, 5-methylsulfonylamino- and 5-(N,N-dimethylaminosulfonylamino) indole-2-carboxylic acid as seg-B in the presence of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide. The synthetic compounds (2,3 and 5-7) were tested for cytotoxic activity against human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using the MTT assay.

Catalog	Product Name	CAS
BADC-00811	Duocarmycin DM free base	1116745-06-2
BADC-00337	Seco-Duocarmycin TM	1142188-60-0
BADC-00223	Duocarmycin A	118292-34-5
BADC-00362	Duocarmycin B1	124325-93-5
BADC-00341	Seco-Duocarmycin SA	152785-82-5
BADC-00605	Duocarmycin TM	157922-77-5
BADC-00332	Seco-DuocarmycinCN	1613286-54-6
BADC-00333	Seco-DuocarmycinDMG	1613286-55-7
BADC-00609	Duocarmycin MB	1613286-58-0
BADC-00336	Seco-Duocamycin GA	1613286-59-1