7272-84-6 Usage
Description
3-(4-Pyridyl)indole is a cell-permeable indolopyridine compound that acts as a selective, reversible, and ATP-competitive inhibitor of Rho kinase (ROCK) activity with an IC50 of 25 μM. It does not inhibit the activation of Rho kinase and does not affect the in vitro activities of MLCK, PKCα, and SAPK2a/p38α. It is a yellow solid.
Uses
Used in Pharmaceutical Industry:
3-(4-Pyridyl)indole is used as a ROCK-I inhibitor for promoting cell spreading, inhibiting membrane blebbing, and inducing dissolution of actin stress fibers in a wound healing assay. It also inhibits ROCK-II and PRK2, another Rho-dependent kinase, with similar potency, while inhibiting MSK-1 and PKA with relatively weaker potency.
Used in Research Applications:
3-(4-Pyridyl)indole is used as a selective, ATP-competitive inhibitor of Rho kinase (ROCK) activity for studying the roles of ROCKs in diverse cellular functions, including cell adhesion and proliferation, smooth muscle contraction, and stem cell renewal.
Used in Drug Development:
3-(4-Pyridyl)indole is used as a potential therapeutic agent for conditions involving cytoskeletal stability and ROCK activity dysregulation, due to its ability to inhibit ROCK-I and ROCK-II with similar potency.
Biochem/physiol Actions
Cell permeable: yes
references
[1] yarrow j c, totsukawa g, charras g t, et al. screening for cell migration inhibitors via automated microscopy reveals a rho-kinase inhibitor[j]. chemistry & biology, 2005, 12(3): 385-395.[2] amano m, fukata y, kaibuchi k. regulation and functions of rho-associated kinase[j]. experimental cell research, 2000, 261(1): 44-51.
Check Digit Verification of cas no
The CAS Registry Mumber 7272-84-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,2,7 and 2 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 7272-84:
(6*7)+(5*2)+(4*7)+(3*2)+(2*8)+(1*4)=106
106 % 10 = 6
So 7272-84-6 is a valid CAS Registry Number.
InChI:InChI=1/C13H10N2/c1-2-4-13-11(3-1)12(9-15-13)10-5-7-14-8-6-10/h1-9,15H
7272-84-6Relevant articles and documents
Direct synthesis of 3-arylindoles via annulation of aryl hydroxylamines with alkynes
Lamar, Angus A.,Nicholas, Kenneth M.
experimental part, p. 3829 - 3833 (2009/09/08)
3-Arylindoles are produced in moderate to excellent yields from the reaction between aryl hydroxylamines and alkynes catalyzed by 10 mol % iron(II) phthalocyanine [Fe(Pc)]. Terminal and internal alkynes afford 3-aryl substituted indoles exclusively. Elect
Some reactions of pyridinium salts derived from trichloromethylarenes with N- and C-nucleophiles
Belen'kii,Poddubnyi,Luiksaar,Krayushkin
, p. 1172 - 1176 (2007/10/03)
The reaction of N-(4-pyridyl)pyridinium and 4-chloropyridinium salts obtained from 1-trichloromethyl-2,4,6-trimethylbenzene and pyridine with N-nucleophiles such as piperidine and morpholine and with C-nucleophiles such as N,N-dimethylaniline and indole proceeds through hetarylation and gives the corresponding 4-substituted pyridines. N-(α,α-Dichlorobenzyl)pyridinium and N,N'-(α-chlorobenzylidene)bispyridinium salts obtained from trichloromethylbenzene do not undergo hetarylation.
Electrosynthesis of arylpyrroles and -indoles under S(RN)1 conditions
Chahma,Combellas,Thiebault
, p. 366 - 368 (2007/10/02)
Arylpyrroles and -indoles are electrosynthesized via a S(RN)1 type reaction. With pyrrolyl anion, the reaction leads mainly to α-substitution, but β-substitution and disubstitution are also observed. With indolyl anion, the main product corresponds to β-substitution. In both cases, the yield of the main product is higher than 50%.
