65881-14-3 Usage
Description
5-Methylindole-3-acetonitrile, also known as 3-Cyano-5-methylindole, is a chemical compound with the molecular formula C11H9N. It is a substituted indole derivative, characterized by the presence of a methyl group and a nitrile group attached to the indole ring. 5-Methylindole-3-acetonitrile is recognized for its role in organic synthesis and pharmaceutical research, where it serves as a versatile building block for the creation of other chemical compounds. Additionally, 5-Methylindole-3-acetonitrile has garnered interest due to its potential biological activities, such as its anti-proliferative properties, which are being explored for cancer treatment. Its utility extends to acting as a precursor in the synthesis of a variety of organic molecules and pharmaceuticals, highlighting its significance in the realm of organic chemistry and pharmaceutical research.
Uses
Used in Organic Synthesis:
5-Methylindole-3-acetonitrile is utilized as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure, featuring both a methyl and a nitrile group, allows for a wide range of chemical reactions, making it a valuable component in the synthesis of diverse molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 5-Methylindole-3-acetonitrile is employed as a building block for the development of new pharmaceuticals. Its structural attributes and potential biological activities contribute to the design and synthesis of novel drug candidates, particularly those targeting cancer treatment.
Used as a Precursor in Pharmaceutical Synthesis:
5-Methylindole-3-acetonitrile serves as a precursor in the synthesis of various pharmaceuticals. Its presence in the molecular structure of target compounds allows for the exploration of its potential therapeutic effects, including its anti-proliferative properties, which are of interest in the development of cancer treatments.
Used in the Study of Biological Activities:
5-Methylindole-3-acetonitrile is also used in research to investigate its biological activities. Its potential as an anti-proliferative agent is being studied for its application in cancer treatment, where it may contribute to the inhibition of tumor growth and the development of new therapeutic strategies.
Check Digit Verification of cas no
The CAS Registry Mumber 65881-14-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,5,8,8 and 1 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 65881-14:
(7*6)+(6*5)+(5*8)+(4*8)+(3*1)+(2*1)+(1*4)=153
153 % 10 = 3
So 65881-14-3 is a valid CAS Registry Number.
65881-14-3Relevant articles and documents
N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential
Bojarski, Andrzej J.,Bugno, Ryszard,Cie?lik, Paulina,Duszyńska, Beata,Handzlik, Jadwiga,Hogendorf, Adam S.,Hogendorf, Agata,Kaczorowska, Katarzyna,Kurczab, Rafa?,Latacz, Gniewomir,Lenda, Tomasz,Sata?a, Grzegorz,Staroń, Jakub,Szewczyk, Bernadeta
, (2021/08/17)
A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.
Tryptamine Synthesis by Iron Porphyrin Catalyzed C?H Functionalization of Indoles with Diazoacetonitrile
Hock, Katharina J.,Knorrscheidt, Anja,Hommelsheim, Renè,Ho, Junming,Weissenborn, Martin J.,Koenigs, Rene M.
supporting information, p. 3630 - 3634 (2019/02/13)
The functionalization of C?H bonds with non-precious metal catalysts is an important research area for the development of efficient and sustainable processes. Herein, we describe the development of iron porphyrin catalyzed reactions of diazoacetonitrile with N-heterocycles yielding important precursors of tryptamines, along with experimental mechanistic studies and proof-of-concept studies of an enzymatic process with YfeX enzyme. By using readily available FeTPPCl, we achieved the highly efficient C?H functionalization of indole and indazole heterocycles. These transformations feature mild reaction conditions, excellent yields with broad functional group tolerance, can be conducted on gram scale, and thus provide a unique streamlined access to tryptamines.
