10/02/2023 - Page 7 of 13 - Indole Building Blocks

Narayana, B. et al. published their research in Organic Chemistry: An Indian Journal in 2006 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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.Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate

Simple syntheses of 5-fluoro/ chloro/ bromoindole-2-methanols and 5-fluoro/ chloro/ bromoindole-2-aldehydes was written by Narayana, B.;Ashalatha, B. V.;Raj, K. K. Vijaya. And the article was included in Organic Chemistry: An Indian Journal in 2006.Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

Efficient and simple methods for the syntheses of 5-haloindole-2-methanols and 5-haloindole-2-aldehydes have been described. 5-Haloindole-2-methanols were prepared by reduction of Me 5-haloindole-2-carboxylates with sodium borohydride in methanol/ THF media and 5-haloindole-2-aldehydes were prepared from the prepared 5-haloindole-2-methanols by oxidation with pyridinium chlorochromate or chromium trioxide-pyridine prepared in situ. The synthesized compounds were isolated in good yields and characterized by ¹H NMR, ¹³C NMR, FABMS and elemental anal. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate).

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

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).

Spatz, Sydney M. et al. published their research in Industrial & Engineering Chemistry Product Research and Development in 1969 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Related Products of 24407-32-7

Some N-substituted tetrabromophthalimide fire-retardant additives was written by Spatz, Sydney M.;Stone, Herman. And the article was included in Industrial & Engineering Chemistry Product Research and Development in 1969.Related Products of 24407-32-7 This article mentions the following:

A broad variety of tetrabromophthalimides for screening as fire-retardant additives was prepared by reaction of tetrabromophthalic anhydride with aliphatic and aromatic amines, diamines, and hydrazines, thermolysis of di-NH4 tetrabromophthalate, and chem. transformations of tetrabromophthalimides. Preliminary tests of several imides, e.g. tetrabromophthalimide and N-(2-hydroxyethyl)phthalimide, indicate that these additives impart fire-retardancy to poly(vinyl chloride), polyester, and epoxy resins. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Related Products of 24407-32-7).

Wang, Lin et al. published their research in Angewandte Chemie, International Edition in 2020 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Formula: C14H9NO2S

A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar-SOF₃ Compounds was written by Wang, Lin;Cornella, Josep. And the article was included in Angewandte Chemie, International Edition in 2020.Formula: C14H9NO2S This article mentions the following:

A convenient protocol to selectively access various arylsulfur(VI) fluorides from com. available aryl halides in a divergent fashion is presented. Firstly, a novel sulfenylation reaction with the electrophilic N-(chlorothio)phthalimide (Cl-S-Phth) and arylzinc reagents afforded the corresponding Ar-S-Phth compounds Subsequently, the S(II) atom was selectively oxidized to distinct fluorinated sulfur(VI) compounds under mild conditions. Slight modifications on the oxidation protocol permit the chemoselective installation of 1, 3, or 4 fluorine atoms at the S(VI) center, affording the corresponding Ar-SO₂F, Ar-SOF₃, and Ar-SF₄Cl. Of notice, this strategy enables the effective introduction of the rare and underexplored -SOF₃ moiety into various (hetero)aryl groups. Reactivity studies demonstrate that such elusive Ar-SOF₃ can be used as a linchpin for the synthesis of highly coveted aryl sulfonimidoyl fluorides (Ar-SO(NR)F). In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Formula: C14H9NO2S).

Zhang, Ji-Quan et al. published their research in Catalysis Communications in 2020 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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.Product Details of 774-47-0

The synthesis of symmetrical 3,3-Disubstituted oxindoles by phosphine-catalyzed 纬/纬-addition of oxindoles with allenoates was written by Zhang, Ji-Quan;Li, Shu-Min;Wu, Chun-Feng;Wang, Xing-Lan;Wu, Ting-Ting;Du, Yao;Yang, Yuan-Yong;Fan, Ling-Ling;Dong, Yong-Xi;Wang, Jian-Ta;Tang, Lei. And the article was included in Catalysis Communications in 2020.Product Details of 774-47-0 This article mentions the following:

A phosphine-catalyzed 纬/纬-addition of oxindoles I (R¹ = H, 5,7-F₂, 6-OMe, 5-Cl, etc.; R² = Me, Boc, Bn, Ph; R³ = H, R⁴ = H, Ph) and II (R² = acetyl, Boc; R³ = H) with allenoates as Et buta-2,3-dienoate, Me buta-2,3-dienoate, benzyl buta-2,3-dienoate has been developed that enables the efficient synthesis of highly functionalized sym. 3,3-disubstituted oxindoles I (R³ = (2E)-4-ethoxy-4-oxobut-2-en-1-yl, (2E)-4-methoxy-4-oxobut-2-en-1-yl, (2E)-4-benzyloxy-4-oxobut-2-en-1-yl; R⁴ = (2E)-4-ethoxy-4-oxobut-2-en-1-yl, (2E)-4-methoxy-4-oxobut-2-en-1-yl, (2E)-4-benzyloxy-4-oxobut-2-en-1-yl, Ph), II (R³ = (2E)-4-ethoxy-4-oxobut-2-en-1-yl). This protocol features mild reaction conditions and wide functional group tolerance and affords corresponding addition products in good to excellent yields. Besides, have also been investigated the biol. utility of the typical 3,3-disubstituted oxindoles against nine phytopathogenic fungi, and I (R¹ = H, R² = Me, R³ = R⁴ = (2E)-4-ethoxy-4-oxobut-2-en-1-yl; R¹ = 5-Br, R² = Me, R³ = R⁴ = (2E)-4-ethoxy-4-oxobut-2-en-1-yl) and exhibited promising antifungal activities. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Product Details of 774-47-0).

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).

O’Connell, E. J. Jr. et al. published their research in Photochemistry and Photobiology in 1971 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Application In Synthesis of 2-Phenylisoindolin-1-one

Absorption and emission studies of electronic states of N-arylbenzamides was written by O’Connell, E. J. Jr.;Delmauro, M.;Irwin, J.. And the article was included in Photochemistry and Photobiology in 1971.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

Absorption and emission spectra of benzanilide, 1-naphthamide, N-phenylphthalimidine, naphthalene, BzNMePh and AcNHPh were obtained in solvents such as EtOH, benzene and 5:5:2 Et2O-isopentane-EtOH at 298 and 77掳K. Quantum yields were dependent on matrix viscosity and temperature Singlet-triplet splittings for the N-arylbenzamides, determined from the emission spectra, were small for 蟺,蟺* states (鈭?1500 cm-1). Phosphorescence maximum were blue-shifted relative to the fluorescence maximum Intersystem crossing efficiencies were consistent with S1 鈫?S0 radiationless decay. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application In Synthesis of 2-Phenylisoindolin-1-one).

Papa, Veronica et al. published their research in Catalysis Science & Technology in 2020 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Related Products of 5388-42-1

Homogeneous cobalt-catalyzed deoxygenative hydrogenation of amides to amines was written by Papa, Veronica;Cabrero-Antonino, Jose R.;Spannenberg, Anke;Junge, Kathrin;Beller, Matthias. And the article was included in Catalysis Science & Technology in 2020.Related Products of 5388-42-1 This article mentions the following:

The first general and efficient cobalt-catalyzed deoxygenative hydrogenation of amides, e.g., I to amines, e.g., II is presented. The optimal catalytic system based on a combination of [Co(NTf₂)₂] and (p-anisyl)triphos in the presence of [Me, ₃SiOTf] as acidic co-catalyst facilitates the direct hydrogenation of a broad range of amides, e.g., I to the corresponding amines e.g., II under mild conditions. A set of control experiments indicate that, after the initial reduction of the amide carboxylic group to the well-known hemiaminal intermediate, the reaction mainly proceeds through C-O bond cleavage though other pathways might be also involved to a minor extent. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Related Products of 5388-42-1).