22/02/2023 - Page 13 of 66 - Indole Building Blocks

Syed, Deeba N. et al. published their research in Journal of Investigative Dermatology in 2015 | CAS: 172922-91-7

5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Quality Control of 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde

FICZ: A Messenger of Light in Human Skin was written by Syed, Deeba N.;Mukhtar, Hasan. And the article was included in Journal of Investigative Dermatology in 2015.Quality Control of 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde This article mentions the following:

Photosensitization, subsequent to photon absorption by chromophores present in the human skin, appears to be a key mechanism of UV-induced oxidative stress. The tryptophan photoproduct 6-formylindolo[3,2-b]carbazole (FICZ), an aryl hydrocarbon receptor ligand, has been found to be a potent UVA photosensitizer, effective at nanomolar concentrations A novel addition to the family of endogenous photosensitizers, the precise mechanism(s) through which it mediates oxidative stress in UVA exposed skin and its response to the UVB spectrum of the solar UV flux remains unexplored. Further studies related to its functionality in the human skin, its utility as a tool against UV-induced adverse effects, and its role in inflammatory skin diseases will have the potential to open up new avenues in the realms of human skin photobiol. In the experiment, the researchers used many compounds, for example, 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7Quality Control of 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde).

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

Jarapula, Ravi et al. published their research in World Journal of Pharmacy and Pharmaceutical Sciences in 2017 | CAS: 84378-94-9

4-Chloro-5-fluoroindoline-2,3-dione (cas: 84378-94-9) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Synthetic Route of C8H3ClFNO2

Synthesis, in vitro anticancer and molecular docking studies of new bisisatins as anticancer agents was written by Jarapula, Ravi;Rekulapally, Sriram;Cidda, Manasa;Manda, Sarangapani. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2017.Synthetic Route of C8H3ClFNO2 This article mentions the following:

Fifteen sym. bis-schiff base of isatin derivatives were synthesized by reaction of succinic acid hydrazide with various isatins and the synthesized compounds were characterized by spectral anal. The substances were further subjected to in vitro cytotoxicity evaluatation against A549 and MCF-7 cell lines with MTT assay. All the synthesized compounds shown significantly inhibited the growth of MCF-7 cells over the A549 cells and the IC50 values of all the compounds were found between 10.24 and 28.65 渭M. The compound 6j has resulted highest cytotoxicity in the entire series studied, in addition 6d, 6c, 6e and 6n were shown to display moderate activity. Further, mol. docking studies of the ligand’s were done on EGFR using GRIP batch docking method. The compounds 6c, 6d, 6e, 6i, 6j and 6l exhibited good docking (PLP) scores with receptor having Hydrogen, Hydrophobic and Vander Waal’s interactions. In the experiment, the researchers used many compounds, for example, 4-Chloro-5-fluoroindoline-2,3-dione (cas: 84378-94-9Synthetic Route of C8H3ClFNO2).

Wu, Yu et al. published their research in Asian Journal of Organic Chemistry in 2022 | CAS: 83-34-1

3-Methyl-1H-indole (cas: 83-34-1) 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.Name: 3-Methyl-1H-indole

Organocatalytic Enantioselective Construction of Axially Chiral Tetrasubstituted Allenes via 1,6-Addition of Alkynyl Indole Imine Methides with 2-Substituted Indoles was written by Wu, Yu;Yue, Zhibin;Qian, Chenxiao;Chen, Xuling;Li, Fushuai;Li, Pengfei;Li, Wenjun. And the article was included in Asian Journal of Organic Chemistry in 2022.Name: 3-Methyl-1H-indole This article mentions the following:

An organocatalytic construction of axially chiral tetrasubstituted allenes I [R¹ = H, 5-F, 6-OMe, etc.; R² = H, F, Cl, Br; R³ = Me, t-Bu, Ph, etc.; R⁴ = Et, i-Pr, t-Bu, Bn; Ar¹ = Ph, 4-FC₆H₄, 3-FC₆H₄, 3-MeC₆H₄] featuring indole skeletons was established. With the aid of chiral phosphoric acid, alkynyl indole imine methides were formed in situ from 伪-(3-indolyl) propargylic alcs., followed by the asym. 1,6-conjugate addition with 2-substituted indoles, furnishing axially chiral indole-containing tetrasubstituted allenes in generally high yields and enantioselectivities. In the experiment, the researchers used many compounds, for example, 3-Methyl-1H-indole (cas: 83-34-1Name: 3-Methyl-1H-indole).

Darwish, Khaled M. et al. published their research in Journal of Molecular Structure in 2022 | CAS: 20315-68-8

6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (cas: 20315-68-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application In Synthesis of 6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Discovery of tetrahydro-尾-carboline- and indole-based derivatives as promising phosphodiesterase-4 inhibitors: Synthesis, biological evaluation, and molecular modeling studies was written by Darwish, Khaled M.;Abdelwaly, Ahmad;Atta, Asmaa M.;Helal, Mohamed A.. And the article was included in Journal of Molecular Structure in 2022.Application In Synthesis of 6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole This article mentions the following:

Phosphodiesterase-4 (PDE4) is responsible for the selective degradation of the 3′-cyclic phosphate bonds of cAMP. A collection of twenty-three diverse 1,2,3,4-tertahydro-尾-carboline- and indole-based analogs were synthesized and assessed for their inhibitory activity against human PDE4. The compounds were prepared using straightforward procedures and characterized using ¹H- and ¹³C NMR, IR, and mass spectroscopy as well as elemental anal. Fifteen of the prepared compounds exhibited significant inhibitory activity with IC₅₀ values in the lower micromolar to upper nanomolar ranges. The most active compounds also showed good selectivity for PDE4 over the related enzyme family member, PDE5, with either insignificant or null% inhibition of the latter enzyme. The indole-based compounds, 21b (I) and 21c (II), showed the most pronounced PDE4 inhibition with IC₅₀ values of 754 and 664 nM, resp. The PDE4B active site comprises both hydrophobic and solvent-filled pockets. The hydrophobic pocket (Q) includes the invariant purine-selective Gln443 which is critical for cAMP. Below this Gln443 lies Phe446 which acts as a hydrophobic P-clamp stabilizing the ligand aromatic ring system. Mol. docking investigation showed preferential anchoring of the active compounds within the PDE4 active site through interactions between the indole nitrogens and the dimethoxy Ph groups with key residues. Overall, the prepared compounds are novel and simple mols. with good potential for future optimization. Showing satisfactory predicted ADME/safety and drug-likeness properties, compound 21c is considered a promising lead for further optimization towards clin. investigation against inflammatory, auto-immune diseases, or certain types of cancer. In the experiment, the researchers used many compounds, for example, 6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (cas: 20315-68-8Application In Synthesis of 6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole).

Han, Bin et al. published their research in Shock in 2016 | CAS: 172922-91-7

5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Quality Control of 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde

Aryl Hydrocarbon Receptor Activation in Intestinal Obstruction Ameliorates Intestinal Barrier Dysfunction Via Suppression of MLCK-MLC Phosphorylation Pathway was written by Han, Bin;Sheng, Baifa;Zhang, Zhicao;Pu, Aimin;Yin, Jiuheng;Wang, Qimeng;Yang, Kunqiu;Sun, Lihua;Yu, Min;Qiu, Yuan;Xiao, Weidong;Yang, Hua. And the article was included in Shock in 2016.Quality Control of 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde This article mentions the following:

Background: Accumulating evidence suggests that the aryl hydrocarbon receptor (AhR) plays an important role in the maintenance of the function of the intestinal barrier in patients with inflammatory bowel disease and in mouse models. Intestinal obstruction (IO) is a clin. emergency consisting of severe dysfunction of intestinal barrier function, and whether AhR plays a role in the pathogenesis of IO remains unknown but would be highly significant. Methods: Male C57BL/6 mice were subjected to IO and either treated with AhR endogenous agonist 6-formylindolo [3, 2-b] carbazole (FICZ) or left untreated. Intestinal tissue was harvested after 24h. Correspondingly, Caco-2 monolayers were treated with FICZ in the absence or presence of hypoxia in vitro or left untreated. The cells were used after 12h. Results: Damage to the intestinal mucosa was anabatic and intestinal permeability was significantly higher in murine IO and hypoxia-induced Caco-2 models than in controls. Under these conditions the activity of AhR was lower and the fluorescence of zonula occludens-1 (ZO-1) was absent. The increased expression of myosin light chain kinase (MLCK) and phosphorylated MLC (pMLC) indicated that this pathway was open. However, treatment with FICZ caused retention of the tight junction protein ZO-1, alleviated the increase of intestinal permeability, and mitigated epithelial injury. Depletion of AhR by AhR small interfering RNA facilitated the unblocking of the MLCK-pMLC signaling pathway and repressed the protein expression of ZO-1 in vitro. Conclusion: AhR activation can ameliorate epithelial barrier dysfunction induced by IO through the suppression of MLCK-pMLC signaling, suggesting that AhR agonist may be a suitable means of addressing this condition. In the experiment, the researchers used many compounds, for example, 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7Quality Control of 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde).

Wu, Fuhai et al. published their research in Organic & Biomolecular Chemistry in 2022 | CAS: 13544-43-9

6-(Trifluoromethyl)-1H-indole (cas: 13544-43-9) 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.Synthetic Route of C9H6F3N

Rhodium(III)-catalyzed regioselective C(sp²)-H activation of indoles at the C4-position with iodonium ylides was written by Wu, Fuhai;Xiao, Lin;Xie, Hui;Chen, Shao-Yong;Song, Jia-Lin;Zheng, Yi-Chuan;Liu, Yan-Zhi;Zhang, Shang-Shi. And the article was included in Organic & Biomolecular Chemistry in 2022.Synthetic Route of C9H6F3N This article mentions the following:

A Rh(III)-catalyzed C4-selective activation of indoles by using iodonium ylides as carbene precursors was reported. This protocol proceeded under redox neutral reaction conditions and provided important coupling products with good tolerance of functional groups and high yields. In addition, one-pot synthesis and scale-up and mechanistic studies were also conducted. In the experiment, the researchers used many compounds, for example, 6-(Trifluoromethyl)-1H-indole (cas: 13544-43-9Synthetic Route of C9H6F3N).

Yang, Yan-Fang et al. published their research in Tetrahedron in 2014 | CAS: 111258-23-2

Methyl 4-methoxy-1H-indole-2-carboxylate (cas: 111258-23-2) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.SDS of cas: 111258-23-2

Gold(I)-catalyzed rearrangement of alkynylaziridine indoles for the synthesis of spiro-tetrahydro-尾-carbolines was written by Yang, Yan-Fang;Li, Lian-Hua;He, Yu-Tao;Luo, Jian-Yi;Liang, Yong-Min. And the article was included in Tetrahedron in 2014.SDS of cas: 111258-23-2 This article mentions the following:

Functionalized spiro-tetrahydro-尾-carbolines were formed by an efficient gold(I)-catalyzed rearrangement reaction of alkynylaziridine indoles. The reaction involved a Friedel-Crafts type intramol. reaction of alkynylaziridine indoles, following by hydroamination of aminoallene intermediate. In the experiment, the researchers used many compounds, for example, Methyl 4-methoxy-1H-indole-2-carboxylate (cas: 111258-23-2SDS of cas: 111258-23-2).

Kuo, Chung-Wen et al. published their research in International Journal of Hydrogen Energy in 2021 | CAS: 15861-36-6

6-Cyanoindole (cas: 15861-36-6) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 15861-36-6

Composites of platinum particles embedded into poly(6-cyanoindole)/poly(styrenesulfonic acid) for methanol oxidation was written by Kuo, Chung-Wen;Lu, Chih-Wei;Chang, Jeng-Kuei;Chen, Ho-Rei;Wu, Tzi-Yi. And the article was included in International Journal of Hydrogen Energy in 2021.Recommanded Product: 15861-36-6 This article mentions the following:

Poly(6-cyanoindole) (P(CnId)) is blended with poly(styrenesulfonic acid) via doping periods of 1, 10, 20, and 30 s to obtain P(CnId)-1PSS, P(CnId)-10PSS, P(CnId)-20PSS, and P(CnId)-30PSS electrodes, resp. FT-IR studies have revealed that P(CnId) is doped with PSS. Pt particles can be doped into P(CnId)-1PSS, P(CnId)-10PSS, P(CnId)-20PSS, and P(CnId)-30PSS by chronocoulometry (0.15 C) using electrodeposition to acquire P(CnId)-1PSS-Pt, P(CnId)-10PSS-Pt, P(CnId)-20PSS-Pt, and P(CnId)-30PSS-Pt films, resp. For comparative purposes, in this study, Pt particles were deposited into P(CnId) under the same conditions. SEM characterization revealed that platinum distributes more uniformly into the as-prepared P(CnId)-10PSS films. The anodic peak currents could be clearly observed to reach the saturation point at a methanol concentration larger than 0.8 M. A large electrocatalytic current towards methanol oxidation (27 mA cm^-2 mg^-1) was noticed in P(CnId)-10PSS-Pt electrodes in comparison to P(CnId)-Pt without PSS (6.3 mA cm^-2 mg^-1) at +0.86 V (vs. RHE), indicating that the P(CnId)-10PSS-Pt electrode reveals potential applicability as an electrocatalyst support. In the experiment, the researchers used many compounds, for example, 6-Cyanoindole (cas: 15861-36-6Recommanded Product: 15861-36-6).

Grigor’ev, E. I. et al. published their research in Bulletin of Experimental Biology and Medicine in 2002 | CAS: 38101-59-6

(S)-4-Amino-5-(((S)-1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-5-oxopentanoic acid (cas: 38101-59-6) 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.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 (S)-4-Amino-5-(((S)-1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-5-oxopentanoic acid

Possible Involvement of Aqueous Medium in Distant Signal Transmission from Immunoactive Dipeptides was written by Grigor’ev, E. I.;Khavinson, V. Kh.;Kochnev, I. N.;Khaloimov, A. I.;Grigor’ev, A. E.;Malinin, V. V.;Kudryavtseva, T. A.. And the article was included in Bulletin of Experimental Biology and Medicine in 2002.Application In Synthesis of (S)-4-Amino-5-(((S)-1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-5-oxopentanoic acid This article mentions the following:

Possible involvement of aqueous medium in distant signal transmission to target cells through solitons without formation of the ligand-receptor complexes is discussed. Temperature dependence of IR spectra for dipeptide and amino acid solutions in the far and near IR regions are presented, which prove principal possibility of such processes. In the experiment, the researchers used many compounds, for example, (S)-4-Amino-5-(((S)-1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-5-oxopentanoic acid (cas: 38101-59-6Application In Synthesis of (S)-4-Amino-5-(((S)-1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-5-oxopentanoic acid).

Fang, Zhang et al. published their research in European Journal of Organic Chemistry in 2022 | CAS: 480-91-1

Isoindolin-1-one (cas: 480-91-1) 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. 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). Reference of 480-91-1

A New Approach to Isoindolinones: Rhodium(III)-Catalyzed [3+2] Annulation Reactions of N-Methoxybenzamides with Bis(tosylamido)methane was written by Fang, Zhang;Shu, Sai;Zhou, Guanyu;Deng, Zefeng;Huang, Pengcheng;Li, Bao;Zhao, Yingsheng. And the article was included in European Journal of Organic Chemistry in 2022.Reference of 480-91-1 This article mentions the following:

A new approach to the synthesis of isoindolinones I (R = H, Me, OMe, etc.; R¹ = Me, OPh, Cl, etc.; R² = Cl, Me, (cyclopropylmethyl)oxidanyl, etc.; R³ = H, Cl; R⁴ = H, 2-Me, 4-Br, etc.) via direct coupling of N-methoxybenzamides 2R-3R¹-4R²-5R³C₆HC(O)NHOMe and bis(tosylamido)methane (R⁴NH)₂CH₂ with rhodium(III) as catalyst has been developed. The reaction is performed under mild conditions without oxidant, and is compatible with various functional groups. Compared with the previously reported methods for constructing isoindolinone skeletons, this method involves a novel [3+2] cyclization, and affords a wide variety of isoindolinones I in moderate to excellent yields. In the experiment, the researchers used many compounds, for example, Isoindolin-1-one (cas: 480-91-1Reference of 480-91-1).