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1-(pyridin-3-ylmethyl)-1H-indole-3-carbaldehyde is a chemical compound with the molecular formula C17H13NO. It is a yellow solid that belongs to the class of indole derivatives. 1-(pyridin-3-ylmethyl)-1H-indole-3-carbaldehyde is characterized by the presence of a pyridine ring, an indole ring, and an aldehyde functional group, which contribute to its aromatic nature and reactivity in organic reactions. It is commonly used in organic synthesis and as a building block for the preparation of various pharmaceuticals and agrochemicals, due to its diverse biological activities, including anticancer, anti-inflammatory, and antimicrobial properties.

928708-60-5

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928708-60-5 Usage

Uses

Used in Pharmaceutical Industry:
1-(pyridin-3-ylmethyl)-1H-indole-3-carbaldehyde is used as a building block for the synthesis of various pharmaceuticals, leveraging its diverse biological activities such as anticancer, anti-inflammatory, and antimicrobial properties. Its unique chemical structure, featuring aromatic rings and an aldehyde functional group, allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
1-(pyridin-3-ylmethyl)-1H-indole-3-carbaldehyde is used as a precursor in the preparation of agrochemicals, taking advantage of its reactivity and potential biological activities to create compounds that can be employed in pest control, crop protection, and other agricultural applications.
Used in Organic Synthesis:
1-(pyridin-3-ylmethyl)-1H-indole-3-carbaldehyde is used as a versatile intermediate in organic synthesis, due to its characteristic reactivity stemming from the aldehyde functional group and the presence of aromatic rings. This allows chemists to use it in the synthesis of a wide range of organic compounds for various applications, including the development of new materials, dyes, and other specialty chemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 928708-60-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 9,2,8,7,0 and 8 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 928708-60:
(8*9)+(7*2)+(6*8)+(5*7)+(4*0)+(3*8)+(2*6)+(1*0)=205
205 % 10 = 5
So 928708-60-5 is a valid CAS Registry Number.
InChI:InChI=1/C15H12N2O/c18-11-13-10-17(9-12-4-3-7-16-8-12)15-6-2-1-5-14(13)15/h1-8,10-11H,9H2

928708-60-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(pyridin-3-ylmethyl)indole-3-carbaldehyde

1.2 Other means of identification

Product number -
Other names 1-(pyridin-3-ylmethyl)-1H-indole-3-carbaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:928708-60-5 SDS

928708-60-5Relevant articles and documents

Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones

Mashayekhi, Vida,Haj Mohammad Ebrahim Tehrani, Kamaleddin,Azerang, Parisa,Sardari, Soroush,Kobarfard, Farzad

, (2021/09/08)

Based on the structural elements of bioactive indole-based compounds, a series of novel 1-substituted indole-3-carboxaldehyde thiosemicarbazones were synthesized as potential antimycobacterial and anticancer agents. The derivatives were prepared via a two

Synthesis and antimycobacterial activity of novel thiadiazolylhydrazones of 1-substituted indole-3-carboxaldehydes

Haj Mohammad Ebrahim Tehrani, Kamaleddin,Mashayekhi, Vida,Azerang, Parisa,Sardari, Soroush,Kobarfard, Farzad,Rostamizadeh, Kobra

, p. 224 - 236 (2014/02/14)

A series of novel thiocarbohydrazones of substituted indoles and their corresponding thiadiazole derivatives were prepared, and their structures were confirmed by different analytical and spectroscopic methods. The derivatives were prepared by a sequential synthetic strategy including substitution at N-1 position of indole ring by various aliphatic and benzylic substituents, followed by condensation with thiocarbohydrazide, and finally cyclization by triethyl orthoformate. The derivatives were tested for their antimycobacterial activity against Mycobacterium bovis BCG, and the results revealed that among the synthesized compounds, thiadiazole derivatives 4e, 4f, 4n, 4p, 4q, and 4t exhibited the highest activity with IC50 value of 3.91 μg/mL. The results indicate that the thiadiazole moiety plays a vital role in exerting antimycobacterial activity. A series of indole-based thiadiazole derivatives with various substitutions at N-1 position of indole ring have been synthesized and tested for their antimycobacterial activity. Compounds 4e (R = butyl), 4f (R = pentyl), 4n (R = 4-fluorobenzyl), 4p (R = 4-chlorobenzyl), 4q (R = 4-bromobenzyl) and 4t (R = 4-methoxybenzyl) were the most potent derivatives with IC50 value of 3.91 μg/mL.

Design, synthesis and anticancer activity of 4-morpholinothieno[3,2-d]- pyrimidine derivatives bearing arylmethylene hydrazine moiety

Zhu, Wufu,Zhai, Xin,Fu, Qiangqiang,Guo, Fei,Bai, Mei,Wang, Jianqiang,Wang, Haiyan,Gong, Ping

experimental part, p. 1037 - 1045 (2012/10/08)

Three series of 4-morpholinothieno[3,2-d]pyrimidine derivatives containing arylmethylene hydrazine moiety (11a-f, 13a-k and 15a-h) were synthesized and their chemical structures as well as the relative stereochemistry were confirmed. The synthesized compounds were evaluated for their cytotoxicity against three cancer cell lines (H460, HT-29, MDA-MB-231). Most of them exhibited moderate to significant cytotoxicity and high-selectivity against one or more cell lines, especially compounds 11c, 13b, 15f and 15g possessing dramatically increased cytotoxicity as compared with the positive controls, which were further evaluated for six other cancer cell lines and one normal cell line. The most promising compound 11c, bearing 3,4-methylenedioxy phenyl group, showed remarkable cytotoxicity against H460, HT-29 and MDA-MB-231 cell lines with IC50 values of 0.003 μM, 0.42 μM and 0.74 μM, which was 1.6- to 290-fold more potent than GDC-0941.

Design, synthesis and 3D-QSAR analysis of novel 2-hydrazinyl-4- morpholinothieno[3,2-d]pyrimidine derivatives as potential antitumor agents

Zhu, Wufu,Liu, Yajing,Zhai, Xin,Wang, Xiao,Zhu, Yan,Wu, Di,Zhou, Hongyu,Gong, Ping,Zhao, Yanfang

, p. 162 - 175 (2013/01/15)

A series of 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives were synthesized and evaluated for their cytotoxic activities against five cancer cell lines. Most of them exhibited moderate to significant cytotoxic activities and high-selectivity against one or more cell lines, and nearly all of them had higher potency than positive controls against MDA-MB-231 cell line. The most promising compound 15f showed strong cytotoxic activities against H460, HT-29 and MDA-MB-231 cell lines, which were 1.7- to 66.5-folds more active than 2-(1H-Indazol-4-yl)-6-((4-(methylsulfonyl)-1-piperazinyl)methyl)-4-(4- morpholinyl)thieno[3,2-d]pyrimidine(GDC-0941). To investigate the SARs of thieno[3,2-d]pyrimidine derivatives in more details, CoMFA (q2 = 0.436, r2 = 0.937) and CoMSIA (q2 = 0.706, r2 = 0.947) models on H460 cell line were established. The generated 3D-QSAR models can be used for further rational design of novel thienopyrimidines as highly potent and selective cytotoxic agents.

Synthesis and biological evaluation of novel 6-hydrazinyl-2,4-bismorpholino pyrimidine and 1,3,5-triazine derivatives as potential antitumor agents

Zhu, Wufu,Liu, Yajing,Zhao, Yanfang,Wang, Haiyan,Tan, Li,Fan, Weijie,Gong, Ping

, p. 812 - 821,10 (2020/09/09)

A series of 6-hydrazinyl-2,4-bismorpholino pyrimidine and 1,3,5-triazine derivatives (5a-5l and 8a-8o) were synthesized and their chemical structures as well as the relative stereochemistry were confirmed. All the synthesized compounds were evaluated for antiproliferative activity against three cancer cell lines (H460, HT-29, and MDA-MB-231). Several potent compounds were further evaluated against two other cell lines (U87MG, H1975). Most of the prepared compounds, particularly compounds 5c and 5j with IC50 values (0.07 and 0.05 μM, respectively) in the nM range, exhibited moderate to excellent antiproliferative activity and high selectivity against the H460 cancer cell line as compared with compound 1. The most promising compound 5j, possessing a cyano group at the 3-position of the benzene ring, showed strong antiproliferative activity against H460, HT-29, and MDA-MB-231 cell lines with IC50 values of 0.05, 6.31, and 6.50 μM, which were 4.6- to 190.4-fold more active than compound 1 (9.52, 29.24, and 36.21 μM), respectively. Copyright

Design and structure-activity relationships of potent and selective inhibitors of blood coagulation factor Xa

Ewing, William R.,Becker, Michael R.,Manetta, Vincent E.,Davis, Roderick S.,Pauls, Henry W.,Mason, Helen,Choi-Sledeski, Yong Mi,Green, Daniel,Cha, Don,Spada, Alfred P.,Cheney, Daniel L.,Mason, Jonathan S.,Maignan, Sebastien,Guilloteau, Jean-Pierre,Brown, Karen,Colussi, Dennis,Bentley, Ross,Bostwick, Jeff,Kasiewski, Charles J.,Morgan, Suzanne R.,Leadley, Robert J.,Dunwiddie, Christopher T.,Perrone, Mark H.,Chu, Valeria

, p. 3557 - 3571 (2007/10/03)

The discovery of a series of non-peptide factor Xa (FXa) inhibitors incorporating 3-(s)-amino-2-pyrrolidinone as a central template is described. After identifying compound 4, improvements in in vitro potency involved modifications of the liphophilic group and optimizing the angle of presentation of the amidine group to the S1 pocket of FXa. These studies ultimately led to compound RPR120844, a potent inhibitor of FXa (K1 = 7 nM) which shows selectivity for FXa over trypsin, thrombin, and several fibrinolytic serine proteinases. RPR120844 is an effective anticoagulant in both the rat model of FeCl2-induced carotid artery thrombosis and the rabbit model of jugular vein thrombus formation.

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