60706-51-6

Basic information

• Product Name: 9-[2-(1-methylpiperidin-2-yl)ethyl]-9H-carbazole
• CAS NO: 60706-51-6
• Molecular Formula: C₂₀H₂₄N₂
• Molecular Weight: 292.418
• Mol File: 60706-51-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 449.9°C at 760 mmHg
• Flash Point: 225.9°C
• Density: 1.11g/cm³
• Vapor Pressure: 2.75E-08mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: 9-[2-(1-methylpiperidin-2-yl)ethyl]-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[2-(1-methylpiperidin-2-yl)ethyl]-9H-carbazole(60706-51-6)
• EPA Substance Registry System: 9-[2-(1-methylpiperidin-2-yl)ethyl]-9H-carbazole(60706-51-6)

Safety Data

• Hazardous Substances Data: 60706-51-6(Hazardous Substances Data)

Upstream product

• 86-74-8 9H-carbazole 
• 210564-52-6 t-butyl 2-(2-bromoethyl)piperidine-1-carboxylate 
• 50-00-0 formaldehyd 
• 1484-84-0 2(RS)-(2-hydroxyethyl)piperidine 
• 118811-03-3 tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate 
• 58878-37-8 1-methyl-2-(2-chloroethyl)-piperidine hydrochloride 

Relevant articles and documents

Design, synthesis and biological evaluation of bisindole derivatives as anticancer agents against Tousled-like kinases

This study presents the design, synthesis, and characterization of bisindole molecules as anti-cancer agents against Tousled-like kinases (TLKs). We show that compound 2 composed of an indirubin-3′-oxime group linked with a (N-methylpiperidin-2-yl)ethyl moiety possessed inhibitory activity toward both TLK1 and TLK2 in vitro and diminished the phosphorylation level of the downstream substrate anti-silencing function 1 (ASF1) in replicating cells. The treatment of compound 2 impaired DNA replication, slowed S-phase progression, and triggered DNA damage response in replicating cells. Structure optimization further discovered six derivatives exhibiting potent TLK inhibitory activity and revealed the importance of the tertiary amine-containing moiety of the side chain. Moreover, the derivatives 6, 17, 19, and 20 strongly suppressed the growth of triple-negative breast cancer MDA-MB-231 cells, non-small cell lung cancer A549 cells, and colorectal cancer HCT-116 cells, while normal lung fibroblast MRC5 and IMR90 cells showed a lower response to these compounds. Taken together, this study identifies tertiary amine-linked indirubin-3′-oximes as potent anticancer agents that inhibit TLK activity.

A combined ligand- and structure-based approach for the identification of rilmenidine-derived compounds which synergize the antitumor effects of doxorubicin

The clonidine-like central antihypertensive agent rilmenidine, which has high affinity for I1-type imidazoline receptors (I1-IR) was recently found to have cytotoxic effects on cultured cancer cell lines. However, due to its pharmacological effects resulting also from α2-adrenoceptor activation, rilmenidine cannot be considered a suitable anticancer drug candidate. Here, we report the identification of novel rilmenidine-derived compounds with anticancer potential and devoid of α2-adrenoceptor effects by means of ligand- and structure-based drug design approaches. Starting from a large virtual library, eleven compounds were selected, synthesized and submitted to biological evaluation. The most active compound 5 exhibited a cytotoxic profile similar to that of rilmenidine, but without appreciable affinity to α2-adrenoceptors. In addition, compound 5 significantly enhanced the apoptotic response to doxorubicin, and may thus represent an important tool for the development of better adjuvant chemotherapeutic strategies for doxorubicin-insensitive cancers.