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Methyl (2R,8S)-8-(chloromethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)benzo(1,2-b:4,3-b')dipyrrole-2-carboxylate

HCID 147252
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
118292-36-7
Standard SMILES
COC(=O)[C@]1(C)Nc2c(O)cc3c(c2C1=O)[C@H](CCl)CN3C(=O)c1cc2cc(OC)c(OC)c(OC)c2[nH]1
InChIKey
BOGFADYROAVVTF-MZHQLVBMSA-N
Molecular formula
C26H26ClN3O8
Average molar mass
544 g/mol
Monoisotopic mass
543.1408425

Overview

Pyrindamycin A is an alpha-amino acid ester.

Names & identifiers

Preferred name
Methyl (2R,8S)-8-(chloromethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)benzo(1,2-b:4,3-b')dipyrrole-2-carboxylate
IUPAC
methyl (2R,8S)-8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate
English name
Benzo1,2-b:4,3-bdipyrrole-2-carboxylic acid, 8-(chloromethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl-, methyl ester, (2R,8S)-
Molecular formula
C26H26ClN3O8
Molecular weight
543.95

Names & synonyms

Pyrindamycin A118292-36-7methyl (2R,8S)-8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylateVCB7X2SS2ABenzo(1,2-b:4,3-b')dipyrrole-2-carboxylic acid, 8-(chloromethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester, (2R-trans)-Methyl (2R,8S)-8-(chloromethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)benzo(1,2-b:4,3-b')dipyrrole-2-carboxylateMethyl (2R,8S)-8-(chloromethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]benzo[1,2-b:4,3-b']dipyrrole-2-carboxylatemethyl (2R,8S)-8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo(3,2-e)indole-2-carboxylateRefChem:565129BRN 4834144CHEMBL159088orb1708778
Show more names
Duocarmycin C2(2R)-8β-Chloromethyl-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indol-2-ylcarbonyl)benzo[1,2-b:4,3-b']dipyrrole-2α-carboxylic acid methyl esterBenzo1,2-b:4,3-bdipyrrole-2-carboxylic acid, 8-(chloromethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl-, methyl ester, (2R,8S)-
SCHEMBL19493132SCHEMBL29403356BOGFADYROAVVTF-MZHQLVBMSA-NCHEBI:199883AKOS040735857Benzo[1,2-b:4,3-b']dipyrrole-2-carboxylic acid, 8-(chloromethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-, methyl ester, (2R,8S)-DA-67044HY-12458

Database identifiers

CAS
118292-36-7
PubChem CID
147252
DTXSID
DTXSID00152093
ChEMBL
CHEMBL159088
ChEBI
CHEBI:199883
UNII
VCB7X2SS2A
Nikkaji
J330.493K

Properties

Computed structural properties

XLogP
3.3
Topological polar surface area
139 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
9
Rotatable bonds
7
Heavy atoms
38
Formal charge
0
Complexity
955

Physicochemical properties

storage temp.
-20 °C · Store at -20°C
solubility
Soluble in DMSO

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Regulatory Information · 1 item

Benzo[1,2-b:4,3-b']dipyrrole-2-carboxylic acid, 8-(chloromethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-, methyl ester, (2R,8S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.

A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026)

Applications · 1 item

UsesPyrindamycin A is an antibiotic that inhibits DNA synthesis. Pyrindamycin A shows antitumor activities against murine leukemia, exhibits stronger cytotoxic activities towards murine and human tumor cell lines and especially towards doxorubicin-resistant cells, inhibits P388 and P388/ADR cells with the same IC50 of 3.9 μg/ml[1].

Suppliers5 total

上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
范德(北京)生物科技有限责任公司15911056312 · [email protected]
TargetMol中国(陶术生物)15002134094 · [email protected]

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Compound notes

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