117311-14-5

Basic information

• Product Name: 7-methoxy-1,2-dihydrocyclopenta[b]indol-3(4H)-one
• Synonyms: 7-methoxy-1,2-dihydrocyclopenta[b]indol-3(4H)-one
• CAS NO: 117311-14-5
• Molecular Formula: C12H11NO2
• Molecular Weight: 201.22124
• Mol File: 117311-14-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 252 °C
• Boiling Point: 401.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.328±0.06 g/cm3(Predicted)
• PKA: 14.79±0.20(Predicted)
• CAS DataBase Reference: 7-methoxy-1,2-dihydrocyclopenta[b]indol-3(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-methoxy-1,2-dihydrocyclopenta[b]indol-3(4H)-one(117311-14-5)
• EPA Substance Registry System: 7-methoxy-1,2-dihydrocyclopenta[b]indol-3(4H)-one(117311-14-5)

Safety Data

• Hazardous Substances Data: 117311-14-5(Hazardous Substances Data)

Upstream product

• 116998-94-8 cyclopentane-1,2-dione-mono-(4-methoxy-phenylhydrazone) 

Relevant articles and documents

Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: Structure-activity relationships for cytotoxicity and antitumor activity

A large number of aziridinyl quinones represented by series 1-9 were studied with respect to their DT-diaphorase substrate activity, DNA reductive alkylation, cytostatic/cytotoxic activity, and in vivo activity. As a result, generalizations have been made with respect with respect to the following: DT-diaphorase substrate design, DT-diaphorase-cytotoxicity quantitative structure-activity relationship (QSAR), and DNA reductive alkylating agent design. A saturating relationship exists between the substrate specificity for human recombinant DT-diaphorase and the cytotoxicity in the human H460 non-small-cell lung cancer cell line. The interpretation of this relationship is that reductive activation is no longer rate-limiting for substrates with high DT-diaphorase substrate specificities. High DT-diaphorase substrate specificity is not desirable in the indole and cylopent[b]indole systems because of the result is the loss of cancer selectivity along with increased toxicity. We conclude that aziridinyl quinones of this type should possess a substrate specificity (Vmax/KM) -4 s-1 for DT-diaphorase in order not to be too toxic or nonselective. While some DNA alkylation was required for cytostatic and cytotoxic activity by series 1-9, too much alkylation results in loss of cancer selectivity as well as increased in vivo toxicity. Indeed, the most lethal compounds are the indole systems with a leaving group in the 3α-position (like the antitumor agent EO9). We conclude that relatively poor DNA alkylating agents (according to our assay) show the lowest toxicity with the highest antitumor activity.

Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[B]indoles and related compounds

There are disclosed various compounds of the formula below, STR1 where n, X and R1 through R4 are as defined in the specification, which are useful for alleviating various memory dysfunctions characterized by a cholinergic deficit su