Category: indole-building-block

Strengths of Acids in Acetonitrile was written by Kuett, Agnes;Tshepelevitsh, Sofja;Saame, Jaan;Lokov, Maert;Kaljurand, Ivari;Selberg, Sigrid;Leito, Ivo. And the article was included in European Journal of Organic Chemistry in 2021.Reference of 4769-96-4 This article mentions the following:

The equilibrium acidity scale (pK_a scale) in acetonitrile has been supplemented by numerous new compounds and new ΔpK_a measurements. It now contains altogether 231 acids – over twice more than published previously – linked by 569 ΔpK_a measurements and spans between the pK_a values of hydrogen iodide (2.8) and indole (32.57), covering close to 30 orders of magnitude. Measurement results acquired over the last 15 years were added to the scale and new least-squares treatment was carried out. The treatment yielded revised pK_a values for the compounds published previously, with the root mean square difference between revised and previous values 0.04, demonstrating very good stability of the scale. Correlation equations were developed for estimating pK_a values for the studied types of compounds in water, DMSO, DMF, and 1,2-dichloroethane on the basis of pK_a values in acetonitrile. These equations enable predicting pK_a values with an average error around or less than 1 pK_a unit, which is a sufficient accuracy for many applications. The scale is expected to be a useful tool for the widest possible research areas in organic chem., electrochem. power sources, catalysis, etc. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Reference of 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 4769-96-4

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

Transition-Metal-Free Direct Arylation and Esterification Reaction of Unprotected Indolylcarboxylic Acid Derivatives: A New Entry to 2-(1H-Indol-2-yl)-5-(phenylthio)-1,3,4-oxadiazole and Aryl 1H-Indole-2-carboxylates was written by Wang, Dawei;Ge, Chenyang;Yu, Xin;Wan, Huida;Xu, Xiang. And the article was included in Synlett in 2016.Safety of 4-Bromo-1H-indole-2-carboxylic acid This article mentions the following:

An efficient, ligand-free, transition-metal-free, direct arylation and esterification reaction of unprotected indolylcarboxylic acid derivatives with diaryliodonium salts was developed, thus providing a new entry to 2-(1H-indol-2-yl)-5-(phenylthio)-1,3,4-oxadiazole and aryl 1H-indole-2-carboxylate derivatives I (R = H, 4-MeO, 4-F, 5-NO₂, 4-Br; Ar = Ph, 4-MeC₆H₄) with good yields. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Safety of 4-Bromo-1H-indole-2-carboxylic acid).

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Safety of 4-Bromo-1H-indole-2-carboxylic acid

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

Indirubin derivatives protect against endoplasmic reticulum stress-induced cytotoxicity and down-regulate CHOP levels in HT22 cells was written by Kosuge, Yasuhiro;Saito, Hiroaki;Haraguchi, Tatsuki;Ichimaru, Yoshimi;Ohashi, Sachiyo;Miyagishi, Hiroko;Kobayashi, Shunsuke;Ishige, Kumiko;Miyairi, Shinichi;Ito, Yoshihisa. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Formula: C11H11NO2 This article mentions the following:

Indirubin and its derivatives have been reported to exhibit anticancer and anti-inflammatory activities. Recently, some of its derived analogs have been shown to have neuroprotective potential. Endoplasmic reticulum (ER) stress has been demonstrated to contribute to the pathogenesis of various neurodegenerative diseases, whereas the effects of indirubin derivatives on ER stress-induced cell death have not been addressed. In the present study, a series of 44 derivatives of indirubin was prepared to search for a novel class of neuroprotective agents against ER stress-induced neuronal death. The MTT reduction assay indicated that tunicamycin (TM), an inducer of ER stress, significantly decreased the viability of hippocampal neuronal HT22 cells. Among the compounds tested, eight showed significant inhibitory activity against TM-induced cell death. Western blot anal. showed that application of these analogs to the cells simultaneously with TM reduced the TM-induced expression of CHOP, an established mediator of ER stress. The results suggest that the preventive effect of these indirubin derivatives against ER stress-induced neuronal death may be due, at least in part, to attenuation of the CHOP-dependent signaling system. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Formula: C11H11NO2).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Formula: C11H11NO2

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

Quinolone-1-(2H)-ones as hedgehog signalling pathway inhibitors was written by Trinh, Trieu N.;McLaughlin, Eileen A.;Abdel-Hamid, Mohammed K.;Gordon, Christopher P.;Bernstein, Ilana R.;Pye, Victoria;Cossar, Peter;Sakoff, Jennette A.;McCluskey, Adam. And the article was included in Organic & Biomolecular Chemistry in 2016.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A series of quinolone-2-(1H)-ones derived from the Ugi-Knoevenagel three- and four-component reaction were prepared exhibiting low micromolar cytotoxicity against a panel of eight human cancer cell lines known to possess the hedgehog signalling pathway (HSP) components, as well as the seminoma TCAM-2 cell line. A focused SAR study was conducted and revealed core characteristics of the quinolone-2-(1H)-ones required for cytotoxicity. These requirements included a C3-tethered indole moiety, an indole C5-Me moiety, an aliphatic tail or an ester, as well as an addnl. aromatic moiety. Further investigation in the SAG-activated Shh-LIGHT2 cell line with the most active analogs such as 2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-2-(1-methyl-1H-indol-3-yl)-N-(pentan-2-yl)acetamide, 2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-2-(5-methyl-1H-indol-3-yl)-N-(pentan-2-yl)acetamide and Et (2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-2-(5-methyl-1H-indol-3-yl)acetyl)glycinate demonstrated a down regulation of the HSP via a reduction in Gli expression and in the mRNA levels of Ptch₁ and Gli₂ and these compounds returned in cell inhibition values of 11.6, 2.9 and 3.1 μM, resp. making this new HSP-inhibitor pharmacophore amongst the most potent non-Smo inhibitors thus far reported. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Safety of 5-Chloroindole-3-carboxaldehyde

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

Cs₂CO₃-catalyzed alkylation of indoles with trifluoromethyl ketones was written by Liu, Xiao-Dong;Wang, Yi;Ma, Hai-Yan;Xing, Chun-Hui;Yuan, Yu;Lu, Long. And the article was included in Tetrahedron in 2017.Name: 6-Nitro-1H-indole This article mentions the following:

A Cs₂CO₃-catalyzed alkylation reaction of indoles with trifluoromethyl ketones was presented. Both alicyclic and aromatic trifluoromethyl ketones as well as various substituted indoles are compatible with the methodol. Good to excellent yields of the corresponding trifluoromethyl substituted tertiary alcs. 2,2,2-tritrifluoro-1-(1H-indol-3-yl)-ethan-1-ols were acquired as the sole products. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

6-Nitro-1H-indole (cas: 4769-96-4) 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.Name: 6-Nitro-1H-indole

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

Ultrasound-assisted rapid reduction of nitroaromatics to anilines using gallium metal was written by Bento, Ian;Bernaldez, Mabel;Noguchi, Ryden;Kawakami, Joel. And the article was included in Synthetic Communications in 2020.Formula: C8H6N2O2 This article mentions the following:

The reduction of nitroarom. compounds to anilines is widely used throughout organic synthesis. Typical methods of performing this transformation utilize hydrogenation over a pyrophoric catalyst or a finely divided reducing metal, which often affords heterogeneous mixtures that are difficult to purify. Herein, for the first time gallium metal is used as a reducing agent in organic synthesis. The reaction proceeds under aerobic conditions and affords homogeneous mixtures for a convenient workup. Using this method, twelve anilines were obtained in 33% to quant. yields with short reaction times of 10-60 min. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C8H6N2O2

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

The First Potent and Selective Non-Imidazole Human Histamine H₄ Receptor Antagonists was written by Jablonowski, Jill A.;Grice, Cheryl A.;Chai, Wenying;Dvorak, Curt A.;Venable, Jennifer D.;Kwok, Annette K.;Ly, Kiev S.;Wei, Jianmei;Baker, Sherry M.;Desai, Pragyna J.;Jiang, Wen;Wilson, Sandy J.;Thurmond, Robin L.;Karlsson, Lars;Edwards, James P.;Lovenberg, Timothy W.;Carruthers, Nicholas I.. And the article was included in Journal of Medicinal Chemistry in 2003.Application In Synthesis of 4-Bromo-1H-indole-2-carboxylic acid This article mentions the following:

Following the discovery of the human histamine H₄ receptor, a high throughput screen of our corporate compound collection identified a potential lead compound Investigation of the structure-activity relationship (SAR) resulted in the discovery of novel compounds, which are the first potent and selective histamine H₄ receptor antagonists to be described. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Application In Synthesis of 4-Bromo-1H-indole-2-carboxylic acid).

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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. 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 4-Bromo-1H-indole-2-carboxylic acid

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

Direct Catalytic Asymmetric Synthesis of Oxindole-Derived δ-Hydroxy-β-ketoesters by Aldol Reactions was written by Zhang, Dongxin;Chen, Yan;Cai, Hu;Yin, Lei;Zhong, Junchao;Man, Jingjing;Zhang, Qian-Feng;Bethi, Venkati;Tanaka, Fujie. And the article was included in Organic Letters in 2020.Category: indole-building-block This article mentions the following:

Direct asym. synthesis of δ-hydroxy-β-ketoesters was accomplished via regio- and enantioselective aldol reactions of β-ketoesters with isatins catalyzed by cinchona alkaloid thiourea derivatives The C-C bond formation of the reactions occurred only at the γ-position of the β-ketoesters. Reaction progress monitoring and product stability analyses under the conditions that included the catalyst indicated that the γ-position reaction products were formed kinetically. Various δ-hydroxy-β-ketoesters bearing 3-alkyl-3-hydroxyoxindole cores relevant to the development of bioactive mols. were synthesized. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Category: indole-building-block).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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). Category: indole-building-block

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

Ligand-Free Copper-Catalyzed One-Pot Synthesis of Indole-2-carboxylic Esters was written by Zhu, Zhiqiang;Yuan, Jiangjun;Zhou, Yirong;Qin, Yang;Xu, Jingshi;Peng, Yiyuan. And the article was included in European Journal of Organic Chemistry in 2014.Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

A simple, efficient, and facile synthetic route for the preparation of indole-2-carboxylic esters was described. The cascade reactions of 2-bromobenzaldehyde and glycine ester hydrochloride were promoted by Cu₂O and a base to provide the corresponding products in good yields. Com. available, inexpensive substrates and reagents were employed under mild reaction conditions in this one-pot operation, which is complementary to existing methods for access to 2-substituted indoles. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate

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

N-Pyridinyl(methyl)-indole-1- or 3-propanamides and propenamides acting as topical and systemic inflammation inhibitors was written by Dassonville, Alexandra;Lardic, Morgane;Breteche, Anne;Nourrisson, Marie Renee;Le Baut, Guillaume;Grimaud, Nicole;Petit, Jean-Yves;Duflos, Muriel. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2008.Reference of 6639-06-1 This article mentions the following:

In this study, the synthetic way to new N-pyridinyl(methyl)indolylpropanamides acting as non acidic NSAIDs has been described. Pharmacomodulation was carried out at N1 and C5 of the indole ring and at the level of the propanamide chain. N3-pyridinylmethyl-[1(4-chlorobenzyl-5-chloroindol-3-yl)propanamide represents one of the most potent compounds in the TPA-induced mouse ear swelling assay, with a level of activity higher than that of ibuprofen and comparable to that of dexamethasone. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Reference of 6639-06-1).

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Reference of 6639-06-1

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