Day: February 23, 2023

Catalyst-free system for sulfenylation of free (N–H) indoles with 2,2′-dithiosalicylic acid under alkaline conditions was written by Zhou, Xiaofei;Li, Xinhua. And the article was included in RSC Advances in 2014.Synthetic Route of C8H6FN This article mentions the following:

A catalyst-free system for the sulfenylation of free (N–H) indoles using 2,2′-dithiosalicylic acid under alk. conditions was reported. The system provided a green, convenient and efficient synthesis of sulfenylindoles I [R = 4-Me, 7-F, 5-Br, etc.], with good yields and high selectivity. The synthesis was performed in a green solvent (isopropanol and H₂O) under atm. and catalyst-free conditions. The procedure was suitable for use with N-unprotected indoles. An electrophilic coupling mechanism was proposed. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Synthetic Route of C8H6FN).

7-Fluoroindole (cas: 387-44-0) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Synthetic Route of C8H6FN

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

Synthesis, biological evaluation, X-ray molecular structure and molecular docking studies of RGD mimetics containing 6-amino-2,3-dihydroisoindolin-1-one fragment as ligands of integrin 伪_IIb尾₃ was written by Krysko, Andrei A.;Samoylenko, Georgiy V.;Polishchuk, Pavel G.;Fonari, Marina S.;Kravtsov, Victor Ch.;Andronati, Sergei A.;Kabanova, Tatyana A.;Lipkowski, Janusz;Khristova, Tetiana M.;Kuz’min, Victor E.;Kabanov, Vladimir M.;Krysko, Olga L.;Varnek, Alexandre A.. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Quality Control of 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid This article mentions the following:

Acylaminooxoisoindolealkanoic acid RGD mimetics such as tetrahydroisoquinolinecarbonylamino oxoisoindolylpropanoic acid I鈥Cl were prepared as integrin 伪_IIb尾₃ ligands for inhibiting platelet aggregation for potential use as antithrombotic agents. The inhibition of platelet aggregation by the oxoisoindolealkanoic acids was determined, and for some compounds, the inhibition of fluorescein-labeled fibrinogen binding to human platelets (and thus to integrin 伪_IIb尾₃) was also determined; for example, I鈥Cl inhibited platelet aggregation with an IC₅₀ value of 1.1 渭M and inhibited the binding of fluorescein-labeled fibrinogen to platelets with an IC₅₀ value of 6.5 nM. Mol. docking calculations of eight of the prepared compounds bound to integrin 伪_IIb尾₃ were performed, indicating the key interactions present; correlations between docking scores and binding affinities were also found. Of the motifs tried, the use of an N-terminal tetrahydroisoquinolinecarbonyl group and a C-terminal 尾-alanine moiety provided the most effective platelet aggregation inhibitors. The structures for a Me aminooxoisoindolebutanoate, a tetrahydroisoquinolinedicarboxylic acid mono-tert-Bu ester, and solvates, salts, or free bases of five of the oxoisoindolealkanoic acids prepared including I鈥₂O were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4Quality Control of 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid).

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid

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

Soybean oligosaccharides combined with probiotics reduce faecal odour compound content by improving intestinal microbiota in pigs was written by Du, Lei;Qiu, Xiaoyu;Zhu, Siyuan;Liu, Jingbo;Wang, Jing;Wang, Qi;Liu, Zuohua;Yang, Feiyun;Yun, Tingting;Qi, Renli. And the article was included in Journal of Animal Physiology and Animal Nutrition.Category: indole-building-block This article mentions the following:

As a potential prebiotic, soybean oligosaccharides (SBOS) can improve animal health by modulating gut microbiota. The aim of this study was to investigate the different effects of supplementing SBOS and supplementing SBOS plus probiotic on the growth and health of pigs. Three groups of growing pigs (n = 12) were fed with basal diet (Control), basal diet + 0.5% SBOS (SBOS), or basal diet +0.5% SBOS + 0.1% compound probiotics (SOP) for 42 days. Results showed that SBOS and SOP treatments had pos. effects on the pigs in the experiment, and the latter was more effective. Compared with the control pigs, the average daily gain of SBOS group and SOP group slightly increased, SOP significantly increased the serum levels of growth hormone and thyroid hormone T3. Importantly, serum concentrations of Ig (IgA, IgG and IgM), total antioxidant capacity and superoxide dismutase in both treatments were increased significantly, SOP group most. Moreover, the faecal odor compounds of pigs, especially skatole, were significantly reduced by the treatments. Addnl., SOP significantly increased the diversity and richness of the faecal microbiota, both the treatments increased genera of norank_f_Muribaculaceae and Ruminococcaceae but reduced Lactobacillus. Correlation anal. indicated that Lactobacillus was significantly pos. correlated with odor compounds, while Ruminococcaceae was the opposite. Conclusively, synbiotics combined with SBOS and probiotics had stronger promotion effects on the growth and health of pigs. In the experiment, the researchers used many compounds, for example, 3-Methyl-1H-indole (cas: 83-34-1Category: indole-building-block).

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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Category: indole-building-block

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

Novel Indolylindazolylmaleimides as Inhibitors of Protein Kinase C-尾: Synthesis, Biological Activity, and Cardiovascular Safety was written by Zhang, Han-Cheng;Derian, Claudia K.;McComsey, David F.;White, Kimberly B.;Ye, Hong;Hecker, Leonard R.;Li, Jian;Addo, Michael F.;Croll, Diane;Eckardt, Annette J.;Smith, Charles E.;Li, Quan;Cheung, Wai-Man;Conway, Bruce R.;Emanuel, Stuart;Demarest, Keith T.;Andrade-Gordon, Patricia;Damiano, Bruce P.;Maryanoff, Bruce E.. And the article was included in Journal of Medicinal Chemistry in 2005.Recommanded Product: 18372-22-0 This article mentions the following:

Novel indolylindazolylmaleimides were synthesized and examined for kinase inhibition. Low-nanomolar inhibitors of PKC-尾 with good to excellent selectivity vs other PKC isoenzymes and GSK-3尾 were identified. In a cell-based functional assay, the title compounds I [R = 2-naphthyl, 3-quinolinyl] effectively blocked IL-8 release induced by PKC-尾II (IC₅₀ = 20-25 nM). In cardiovascular safety assessment, representative lead compounds bound to the hERG channel with high affinity, potently inhibited ion current in a patch-clamp experiment, and caused a dose-dependent increase of QT_c in guinea pigs. In the experiment, the researchers used many compounds, for example, Methyl 2-(1H-indol-3-yl)-2-oxoacetate (cas: 18372-22-0Recommanded Product: 18372-22-0).

Methyl 2-(1H-indol-3-yl)-2-oxoacetate (cas: 18372-22-0) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Recommanded Product: 18372-22-0

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

Behavioral effects of benzodiazepine antagonists in chlordiazepoxide tolerant and non-tolerant rats was written by Takada, K.;Suzuki, T.;Hagen, T.;Cook, J. M.;Katz, J. L.. And the article was included in Life Sciences in 1989.COA of Formula: C16H16N2O2 This article mentions the following:

Rats were trained to respond under 3-min fixed-interval schedules of food presentation, and effects of the benzodiazepine-receptor ligands, flumazenil, 2-(4-methoxyphenyl)pyrazolo[4,3-c]quinolin-3(5H)-one (CGS 9895), 3-carbo-t-butoxy-尾-carboline (尾-CCtB), and 尾-carboline-3-carboxylic acid Et ester (尾-CCE) were assessed before and after the induction of tolerance to chlordiazepoxide. Before daily administration of chlordiazepoxide, none of the antagonists produced appreciable effects on rates of responding up to doses of 32.0 mg/kg i.p. 尾-CCE was the only antagonist studied at a higher dose (100.0 mg/kg i.p.), which decreased response rates. After 23 days of daily chlordiazepoxide administration (oral doses started at 10 and increased to 100 mg/kg/day by the 17th day), dose-effect curves for chlordiazepoxide were shifted to the right by about one-half log unit. Subjects were also more sensitive to the flumazenil, CGS 9895, and 尾-CCtB; however, since these drugs produced only small effects in non-tolerant subjects, precise estimates of the degree of the shift in dose-effect curves could not be estimated However, there were differences in the changes in the dose-effect curves induced by chlordiazepoxide tolerance. These results suggest differences in mechanism of action of antagonists in tolerant and non-tolerant subjects, and further that the sensitivity that is induced to antagonists in tolerant subjects is not conferred equally to all drugs having benzodiazepine antagonist activity. In the experiment, the researchers used many compounds, for example, tert-Butyl 9H-pyrido[3,4-b]indole-3-carboxylate (cas: 93835-05-3COA of Formula: C16H16N2O2).

tert-Butyl 9H-pyrido[3,4-b]indole-3-carboxylate (cas: 93835-05-3) 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.COA of Formula: C16H16N2O2

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

Indexing molecules for their hERG liability was written by Rayan, Anwar;Falah, Mizied;Raiyn, Jamal;Da’adoosh, Beny;Kadan, Sleman;Zaid, Hilal;Goldblum, Amiram. And the article was included in European Journal of Medicinal Chemistry in 2013.Application In Synthesis of rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate This article mentions the following:

The human Ether-a-go-go-Related-Gene (hERG) potassium (K⁺) channel is liable to drug-inducing blockage that prolongs the QT interval of the cardiac action potential, triggers arrhythmia and possibly causes sudden cardiac death. Early prediction of drug liability to hERG K⁺ channel is therefore highly important and preferably obligatory at earlier stages of any drug discovery process. In vitro assessment of drug binding affinity to hERG K⁺ channel involves substantial expenses, time, and labor; and therefore computational models for predicting liabilities of drug candidates for hERG toxicity is of much importance. In the present study, the authors apply the Iterative Stochastic Elimination (ISE) algorithm to construct a large number of rule-based models (filters) and exploit their combination for developing the concept of hERG Toxicity Index (ETI). ETI estimates the mol. risk to be a blocker of hERG potassium channel. The area under the curve (AUC) of the attained model is 0.94. The averaged ETI of hERG binders, drugs from CMC, clin.-MDDR, endogenous mols., ACD and ZINC, were found to be 9.17, 2.53, 3.3, -1.98, -2.49 and -3.86 resp. Applying the proposed hERG Toxicity Index Model on external test set composed of more than 1300 hERG blockers picked from chEMBL shows excellent performance (Matthews Correlation Coefficient of 0.89). The proposed strategy could be implemented for the evaluation of chems. in the hit/lead optimization stages of the drug discovery process, improve the selection of drug candidates as well as the development of safe pharmaceutical products. In the experiment, the researchers used many compounds, for example, rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate (cas: 115956-12-2Application In Synthesis of rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate).

rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate (cas: 115956-12-2) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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 rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-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

Synthesis of 1-indolyl-3,5,8-substituted 纬-carbolines: one-pot solvent-free protocol and biological evaluation was written by Dudhe, Premansh;Krishnan, Mena Asha;Yadav, Kratika;Roy, Diptendu;Venkatasubbaiah, Krishnan;Pathak, Biswarup;Chelvam, Venkatesh. And the article was included in Beilstein Journal of Organic Chemistry in 2021.HPLC of Formula: 27421-51-8 This article mentions the following:

1,5-Disubstituted indole-2-carboxaldehyde derivatives and glycine alkyl esters underwent a novel cascade imination-heterocylization in the presence of the organic base DIPEA to provide 1-indolyl-3,5,8-substituted 纬-carbolines I [R¹ = H, MeO, Ph; R² = Me, benzyl, tosyl, etc.; R³ = MeOOC, EtOOC, t-BuOOC] and II in good yields. The 纬-carbolines I and II are fluorescent and exhibited anticancer activities against cervical, lung, breast, skin and kidney cancer cells. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indole-2-carbaldehyde (cas: 27421-51-8HPLC of Formula: 27421-51-8).

1-Methyl-1H-indole-2-carbaldehyde (cas: 27421-51-8) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.HPLC of Formula: 27421-51-8

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

Visible-light promoted synthesis of 3-arylthioindoles from indoles and diaryl disulfides was written by Ye, Lin-miao;Chen, Jie;Mao, Peng;Zhang, Xue-jing;Yan, Ming. And the article was included in Tetrahedron Letters in 2017.Application of 1076-74-0 This article mentions the following:

3-Arylthioindoles, e.g., I, could be synthesized in good yields via the photoirradiation of indoles and disulfides. The reaction is efficiently promoted by the catalytic amount of sodium iodide. A reaction mechanism involving the electrophilic substitution of indoles with arylsulfenyl iodine intermediates is suggested. In the experiment, the researchers used many compounds, for example, 5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0Application of 1076-74-0).

5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application of 1076-74-0

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

Synthesis of 5-methoxy-2, 3-dimethyl-1H-indole was written by Sun, Ming-na;Zhou, Yi;Zhang, Pei-quan;Wang, Sheng;Sun, Ming-jiao. And the article was included in Huaxue Shiji in 2019.Reference of 1076-74-0 This article mentions the following:

The title compound was synthesized from 5-methoxy-2-methyl-1H-indole by a Vilsmeier-Haack reaction and a reduction reaction. 5-Methoxy-2-methyl-1H-indole was firstly converted to 5-methoxy-2-methyl-1H-indole-3-carboxaldehyde via a Vilsmeier-Haack reaction. The latter intermediate was subjected to sodium cyanoborohydride and acetic acid in THF to synthesize the target compound, which was confirmed by ¹HNMR, ¹³CNMR and MS. This method has considerable advantages in terms of the use of easily available raw material, simple operation, mild reaction conditions and high yield. The title compound is an important organic intermediate, and is widely used in the field of medicine. In the experiment, the researchers used many compounds, for example, 5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0Reference of 1076-74-0).

5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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.Reference of 1076-74-0

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