827-01-0 | - Indole Building Blocks

Basarab, Gregory S. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2008 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of 5-Chloroindole-3-carboxaldehyde

Design of Helicobacter pylori glutamate racemase inhibitors as selective antibacterial agents: A novel pro-drug approach to increase exposure was written by Basarab, Gregory S.;Hill, Pamela J.;Rastagar, Abdullah;Webborn, Peter J. H.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

High-throughput screening uncovered a pyrazolopyrimidinedione hit as a selective, low micromolar inhibitor of Helicobacter pylori glutamate racemase (MurI). Variation of the substituents around the scaffold led to low nanomolar inhibitors and improved antibacterial activity. The challenge in this program was to translate excellent enzyme inhibition into potent antibacterial activity and pharmacokinetics suitable for oral therapy. Compounds were profiled for MurI inhibition, activity against H. pylori, microsomal stability, and pharmacokinetics in mice. Iterative cycles of analog synthesis and biol. testing led to compounds with substituents optimized for both low MICs (鈮? 渭g/mL) and good microsomal stability. In order to achieve high bioavailability, a novel pro-drug approach was implemented wherein a solubilizing sulfoxide moiety is oxidized in vivo to a sulfone. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Ravi, Ch. et al. published their research in Russian Journal of Bioorganic Chemistry in 2019 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Product Details of 827-01-0

Induction of Apoptosis in SKOV3 and DNA Binding by Cobalt(III) Polypyridyl Complexes was written by Ravi, Ch.;Vuradi, Ravi Kumar;Avudoddi, Srishailam;Ramchander, M.;Satyanarayana, S.. And the article was included in Russian Journal of Bioorganic Chemistry in 2019.Product Details of 827-01-0 This article mentions the following:

Abstract: Three new Co(III) polypyridyl complexes [Co(phen)₂CIIP]³⁺ {CIIP = 2-(5-chloro-3a,H-isoindol-3-yl)-1H-imidazo[4,5-f][1,10]phenantholine} (phen = 1,10 phenanthroline), [Co(bpy)₂CIIP]³⁺ (bpy = 2,2′-bipyridine), and [Co(dmb)₂CIIP]³⁺ (dmb = 4,4′-dimethyl-2,2′-bipyridine) were synthesized and characterized by different spectral methods. The complexes interact with DNA in an intercalation mode as confirmed by spectroscopic titration and viscosity measurements. All three complexes cleaved the pBR322 DNA in photoactivated cleavage studies and exhibited good antimicrobial activity. Anticancer activity of these Co(III) complexes was evaluated on the SKOV3 cell line. Cytotoxicity by MTT assay showed growth inhibition in dose dependent manner. Cell cycle anal. by flow cytometry data showed increase in Sub G1 population. Annexin V FITC/PI staining confirmed that these complexes caused cell death by the induction of apoptosis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Product Details of 827-01-0).

Lu, Lin et al. published their research in Tetrahedron in 2015 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Category: indole-building-block

Iodine-catalyzed C3-formylation of indoles via C-N bond cleavage of tertiary amines under aerobic conditions was written by Lu, Lin;Xiong, Qiheng;Guo, Shengmei;He, Tianqiang;Xu, Feng;Gong, Jiuhan;Zhu, Zheng;Cai, Hu. And the article was included in Tetrahedron in 2015.Category: indole-building-block This article mentions the following:

A novel route was developed for the C3-formation of indoles using iodine as the catalyst. This transformation involves the cleavage of the C-N bond of tertiary amines by the Cross-Dehydrogenative Coupling reaction (CDC), and is well tolerated by a range of 1H-indoles under aerobic conditions. Moreover, this method can be applied to gram-scale synthesis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Category: indole-building-block).

Rahimi, Alireza et al. published their research in Synthesis in 2010 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.SDS of cas: 827-01-0

Tandem Suzuki-Miyaura cross-coupling/dehydrobromination of 1,1-dibromoalkenes to alkynes with a cyclobutene-1,2-diylbis(imidazolium) salt as catalyst precursor was written by Rahimi, Alireza;Schmidt, Andreas. And the article was included in Synthesis in 2010.SDS of cas: 827-01-0 This article mentions the following:

A cyclobutene-1,2-bis(imidazolium) salt proved to be an efficient catalyst precursor for 1-pot tandem Suzuki-Miyaura/dehydrobromination reactions for the synthesis of alkynes starting from 1,1-dibromo alkenes and Pd(OAc)₂, arylboronates, and KOCMe₃ in PhMe. Starting materials were prepared from aldehydes under Corey-Fuchs conditions. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0SDS of cas: 827-01-0).

Ma, Jinhui et al. published their research in Organic Letters in 2021 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde

Access to Polycyclic Thienoindolines via Formal [2+2+1] Cyclization of Alkynyl Indoles with S₈ and K₂S was written by Ma, Jinhui;Luo, Jiajun;Jiang, Kai;Zhang, Guangwen;Liu, Shubin;Yin, Biaolin. And the article was included in Organic Letters in 2021.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Herein, a protocol for accessing polycyclic dihydrothiophenes I (R¹ = H, 10-F, 9-Cl, 8-Br, etc.; R² = Ph, 4-FC₆H₄, 3,4-Me₂C₆H₄, etc.; R³ = Et, i-Pr, n-Pr, PhCH₂; R⁴ = H, Me) by means of formal [2+2+1] intramol. dearomatizing cyclization of alkynyl indoles II with K₂S and S₈ as the sources of sulfide is reported. In addition, tetrahydrothienoindolines III (R¹-R³ as above) were stereoselectively synthesized from the corresponding II (R⁴ = H) via a one-pot, two-step protocol involving AgNO₃-catalyzed alkenyl dearomatization followed by two nucleophilic addition reactions involving K₂S. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application In Synthesis of 5-Chloroindole-3-carboxaldehyde).

Duan, Shengguo et al. published their research in Advanced Synthesis & Catalysis in 2020 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C9H6ClNO

Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles was written by Duan, Shengguo;An, Yuehui;Xue, Bing;Chen, Yidian;Zhang, Wan;Xu, Ze-Feng;Li, Chuan-Ying. And the article was included in Advanced Synthesis & Catalysis in 2020.Formula: C9H6ClNO This article mentions the following:

Acyloxy-substituted 伪,尾-unsaturated imines generated in-situ from triazoles acts as aza-[4C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system included operational simplicity, readily available substrates, construction of sterically demanding quaternary centers and convenient derivatization using triflate. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Formula: C9H6ClNO).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C9H6ClNO

Islam, Mohammad Shahidul et al. published their research in Journal of Molecular Structure in 2022 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). SDS of cas: 827-01-0

Synthesis, molecular docking and enzyme inhibitory approaches of some new chalcone-engrafted pyrazoles as potential antialzheimer, antidiabetic and antioxidant agents was written by Islam, Mohammad Shahidul;Al-Majid, Abdullah Mohammed;Sholkamy, Essam Nageh;Yousuf, Sammer;Ayaz, Muhammad;Nawaz, Asif;Wadood, Abdul;Rehman, Ashfaq Ur;Verma, Ved Prakash;Bari, Ahmed;Haukka, Matti;Soliman, Saied M.;Barakat, Assem. And the article was included in Journal of Molecular Structure in 2022.SDS of cas: 827-01-0 This article mentions the following:

A series of pyrazole-based chalcones I (R = Ph, 3-MeC₆H₄, 2-benzothienyl, 3-indolyl, 5-chloro-3-methyl-1-phenylpyrazol-4-yl, etc.) was designed and constructed in two steps from readily available acetylacetone, phenylhydrazine and DMF-DMA as starting materials. The synthesized chalcone analogs were screened for in vitro anti-acetylcholinesterase potential, antidiabetic potential against 伪-glucosidase and 伪-amylase, and antioxidant potentials against DPPH free radicals. The compounds I (R = ferrocenyl, Ph, 1-naphthyl, 3-BrC₆H₄, 3-O₂NC₆H₄) showed strongest acetylcholine esterase inhibition (AChEI) with IC₅₀ values of 5 卤 1.16渭g/mL, 8 卤 0.14渭g/mL, 8 卤 0.57渭g/mL, 10 卤 1.73渭g/mL and 10 卤 0.60渭g/mL, resp. The highest inhibition against 伪-glucosidase was demonstrated by compounds I (R = 4-ClC₆H₄, 3-O₂NC₆H₄, 3-FC₆H₄, 4-MeOC₆H₄, 3-MeC₆H₄, Ph) with IC₅₀ values of 4 卤 0.14, 6 卤 0.43, 8 卤 0.43, 10 卤 0.11, 11 卤 0.28 and 12 卤 0.57渭g/mL, resp., whereas, the compounds I (R = 5-bromo-3-indolyl, benzothiophen-2-yl, 1-methyl-3-indolyl, 5-chloro-3-indolyl, 5-chloro-3-methyl-1-phenylpyrazol-4-yl) showed prominent 伪-amylase inhibition with IC₅₀ values of 20 卤 1.15渭g/mL, 30 卤 0.60渭g/mL, 40 卤 0.72渭g/mL, 40 卤 0.50渭g/mL, and 60 卤 2.19渭g/mL, resp.. The highest anti-oxidant potential against DPPH free radicals was demonstrated by compounds I (R = 1-methyl-3-indolyl, 3-indolyl, 5-chloro-3-indolyl) with IC₅₀ values of 160 卤 5.77, 260 卤 4.63, and 360 卤 4.04渭g/mL, resp. Mol. docking was used to study their interaction with the active site of enzymes. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0SDS of cas: 827-01-0).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). SDS of cas: 827-01-0

Kang, Bohee et al. published their research in Bioorganic & Medicinal Chemistry in 2015 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde

3-Benzamides and 3,4,5-trimethoxyphenyl amines as calcium channel blockers was written by Kang, Bohee;Oh, Jung Ae;Lee, Jee Youn;Rhim, Hyewhon;Yune, Tae Young;Park Choo, Hea-Young. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

T- and N-type calcium channels have known for relating to therapy of neuropathic pain which is chronic, debilitating pain state. Neuropathic pain is caused by damage of the somatosensory system. It may be associated with abnormal sensations and pain produced by normally non-painful stimuli (allodynia). Neuropathic pain is very difficult to treat, and only some 40-60% of patients achieve partial relief. For a neuropathic pain therapy, anticonvulsant like Lamotrigine, Carbamazepine and a topical anesthetic such as Lidocaine are used. We synthesized 15 novel amine derivatives and evaluated their activities against T-type and N-type calcium channels by whole-cell patch clamp recording on HEK293 cells. Among the tested compounds, compound 10 showed good inhibitory activity for both T-type and N-type calcium channels with the IC₅₀ value of 1.9 渭M and 4.3 渭M, resp. Compound 10 also showed good analgesic activity on rat spinal cord injury model. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application In Synthesis of 5-Chloroindole-3-carboxaldehyde).

Bu, Ming et al. published their research in Huaxue Shiji in 2019 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Formula: C9H6ClNO

Synthesis and antitumor activity of 5伪, 8伪-peroxide steroid derivatives containing dihydrazone unit was written by Bu, Ming;You, Dan;Zhang, Song;Chen, Zhe. And the article was included in Huaxue Shiji in 2019.Formula: C9H6ClNO This article mentions the following:

Using dehydroepiandrosterone (DHEA) as staring material, five steroidal endoperoxide derivatives with different indole side chain structures had been synthesized, and the structures were confirmed by MS, ¹HNMR and ¹³CNMR. The antiproliferative activity was evaluated against human liver carcinoma cells (HepG2), human breast cancer cells (MCF-7) and normal kidney epithelial cells (293 T). The results showed that 5伪,8伪-epidioxy-17-(5-fluoro-indol-3-ylmethylene) hydrazonoandrostan-3尾-ol and 5伪,8伪-epidioxy-17-(5-chloro-indol-3-ylmethylene) hydrazonoandrostan-3尾-ol had significant inhibitory activity to the tested cancer cells. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Formula: C9H6ClNO).

Blough, Bruce E. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2014 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Computed Properties of C9H6ClNO

Alpha-ethyltryptamines as dual dopamine-serotonin releasers was written by Blough, Bruce E.;Landavazo, Antonio;Partilla, John S.;Decker, Ann M.;Page, Kevin M.;Baumann, Michael H.;Rothman, Richard B.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2014.Computed Properties of C9H6ClNO This article mentions the following:

The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT_2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were >10-fold less potent as NE releasers. Addnl., these compounds had different activity profiles at the 5-HT_2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT_2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Computed Properties of C9H6ClNO).