Tag: 100-200

An investigation into the substituent effect of halogen atoms on the crystal structures of indole-3-carboxylic acid (ICA) was written by Luo, Yang-Hui;Sun, Bai-Wang. And the article was included in CrystEngComm in 2013.Electric Literature of C9H6ClNO This article mentions the following:

A study into the substituent effect of halogen atoms (F, Cl, Br) on the crystal structure of indole-3-carboxylic acid (ICA) was prepared The study was done through the aspect of crystal structure, intermol. interactions and π···π stacking motifs with the assistance of IR spectra, elemental analyses, NMR spectra, DSC, thermogravimetric analyses (TGA) and hot stage microscopy (HSM) measurements. The different kinds of halogen atoms and the different substituted positions have a significant effect on the crystal structures, mol. π···π stacking motifs and the kinds of intermol. interactions. The authors further correlated the m.ps. of the ICAs with the H-H, O-H and X-H (X = F, Cl, Br) interactions, and found a pos. correlation between them. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Electric Literature of C9H6ClNO).

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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Electric Literature of C9H6ClNO

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

Analogs of the Dopamine Metabolite 5,6-Dihydroxyindole Bind Directly to and Activate the Nuclear Receptor Nurr1 was written by Kholodar, Svetlana A.;Lang, Geoffrey;Cortopassi, Wilian A.;Iizuka, Yoshie;Brah, Harman S.;Jacobson, Matthew P.;England, Pamela M.. And the article was included in ACS Chemical Biology in 2021.Reference of 4769-96-4 This article mentions the following:

The nuclear receptor-related 1 protein, Nurr1, is a transcription factor critical for the development and maintenance of dopamine-producing neurons in the substantia nigra pars compacta, a cell population that progressively loses the ability to make dopamine and degenerates in Parkinson’s disease. Recently, we demonstrated that Nurr1 binds directly to and is regulated by the endogenous dopamine metabolite 5,6-dihydroxyindole (DHI). Unfortunately, DHI is an unstable compound, and thus a poor tool for studying Nurr1 function. Here, we report that 5-chloroindole, an unreactive analog of DHI, binds directly to the Nurr1 ligand binding domain with micromolar affinity and stimulates the activity of Nurr1, including the transcription of genes governing the synthesis and packaging of dopamine. 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. 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 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

Effect of heterocyclic ring system on formation of dimeric quinolones under catalyst-free conditions: a green approach was written by Madhu, Bandi;Raja sekar, B.;Venkata Ramana Reddy, C. H.;Dubey, P. K.. And the article was included in Research on Chemical Intermediates in 2017.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

The intermediate-dependent green and efficient synthesis of dimeric quinolones I (R¹ = Me, Et; R² = H, Me, OMe, Cl, Br, NO₂) and II (R³ = Me, Et; R⁴ = Ph, 3-ClC₆H₄, 3,4-(OMe)₂, etc.) was described. Compounds I were prepared by either the Knoevenagel condensation of 4-hydroxy-quinolin-2(1H)-ones with indole-3-carboxaldehydes in water followed by Michael-type addition of the (3-indolylmethylene)quinoline diones under catalyst-free conditions with another equivalent of indole-3-carboxaldehyde or via a one-pot reaction using two equivalent of the aldehyde. Compounds II were prepared by the tandem one-pot Knoevenagel condensation followed by Michael-type addition of 4-hydroxy-quinolin-2(1H)-ones with aromatic aldehydes in water. This reaction was found to be environmentally friendly, has easy-workup and shorter reaction times giving good yields of the product without the need for its isolation using column chromatog. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

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. 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-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

Microwave-induced one pot synthesis of fluorinated spiro [indole-pyrimidines] was written by Sachdeva, Harshita. And the article was included in Indian Journal of Heterocyclic Chemistry in 2009.Quality Control of 7-Nitroindoline-2,3-dione This article mentions the following:

A series of fluorinated spiro[indole-pyrimidines] were synthesized in 75-85% yields by rapid and highly efficient one-pot microwave-induced technique involving condensation of 3-aroylmethylene-2H-indol-ones with fluorinated phenylthioureas using ethanol as energy transfer medium. Aroylmethylene-indolones was synthesized in situ by the reaction of substituted indole-2,3-diones and fluorinated acetophenones. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Quality Control of 7-Nitroindoline-2,3-dione).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Quality Control of 7-Nitroindoline-2,3-dione

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

α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands was written by Ann, Jihyae;Czikora, Agnes;Saini, Amandeep S.;Zhou, Xiaoling;Mitchell, Gary A.;Lewin, Nancy E.;Peach, Megan L.;Blumberg, Peter M.;Lee, Jeewoo. And the article was included in Journal of Medicinal Chemistry in 2018.Name: 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Diacylglycerol-lactones have proven to be a powerful template for the design of potent ligands targeting C1 domains, the recognition motif for the cellular second messenger diacylglycerol. A major objective has been to better understand the structure activity relations distinguishing the seven families of signaling proteins that contain such domains, of which the protein kinase C (PKC) and RasGRP families are of particular interest. Here, we synthesize a series of aryl/alkyl substituted diacylglycerol-lactones and probe their relative selectivities for RasGRP3 vs. PKC. Compound I showed 72.6-fold selectivity relative to PKC alpha and 45.1-fold selectivity relative to PKC epsilon for in vitro binding activity. Likewise, in intact cells compound I induced Ras activation, a downstream response to RasGRP stimulation, with 8-29 fold selectivity relative to PKC delta S299 phosphorylation, a measure of PKC delta stimulation. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Name: 5-Chloroindole-3-carboxaldehyde).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Name: 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

Discovery of IDO1 and DNA dual targeting antitumor agents was written by Fang, Kun;Wu, Shanchao;Dong, Guoqiang;Wu, Ying;Chen, Shuqiang;Liu, Jianhe;Wang, Wei;Sheng, Chunquan. And the article was included in Organic & Biomolecular Chemistry in 2017.Reference of 4769-96-4 This article mentions the following:

The development of small mols. for cancer immunotherapy is highly challenging and indoleamine 2,3-dioxygenase 1 (IDO1) represents a promising target. Inspired by the synergistic effects between IDO1 inhibitors and traditional antitumor chemotherapeutics, the first orally active dual IDO1 and DNA targeting agents were designed by the pharmacophore fusion strategy. The bifunctional hybrids exhibited enhanced IDO1 enzyme inhibitory activity and in vitro cytotoxicity as compared to IDO1 inhibitor 1-methyl-tryptophan and DNA alkylating agent melphalan. In a murine LLC tumor model, the dual targeting agents demonstrated excellent antitumor efficacy, highlighting the advantages of this novel design strategy to improve the efficacy of small mol. cancer immunotherapy. 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. 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.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

Unexpected synthesis of azepino[4,3,2-cd]indoles from 4-aminoindoles was written by Halaiev, Olexandr;Garazd, Myroslav;Gzella, Andrzej;Lesyk, Roman. And the article was included in Tetrahedron Letters in 2017.Quality Control of 1-Methyl-1H-indol-4-amine This article mentions the following:

Synthesis of azepinoindoles I [R = Me, CH(Me)₂, CH₂C₆H₅, etc.] instead of quinolines from the regioselective Skraup-Doebner-Von Miller reaction of 4-aminoindoles and acetone in the presence of hydrochloric acid as a catalyst was developed. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Quality Control of 1-Methyl-1H-indol-4-amine).

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) 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. 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 1-Methyl-1H-indol-4-amine

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

Scaffold-Inspired Enantioselective Synthesis of Biologically Important Spiro[pyrrolidin-3,2′-oxindoles] with Structural Diversity through Catalytic Isatin-Derived 1,3-Dipolar Cycloadditions was written by Shi, Feng;Tao, Zhong-Lin;Luo, Shi-Wei;Tu, Shu-Jiang;Gong, Liu-Zhu. And the article was included in Chemistry – A European Journal in 2012.Product Details of 774-47-0 This article mentions the following:

Catalytic asym. construction of the biol. important spiro[pyrrolidin-3,2′-oxindole] scaffold with contiguous quaternary stereogenic centers in excellent stereoselectivities (up to >99:1 d.r., 98 % ee) has been established by using an organocatalytic 1,3-dipolar cycloaddition of isatin-based azomethine ylides. This protocol represents the first example of catalytic asym. 1,3-dipolar cycloadditions involving azomethine ylides generated in situ from unsym. cyclic ketones. In addition, theor. calculations were performed on the transition state of the reaction to understand the stereochem. Preliminary bioassays with these spiro[pyrrolidin-3,2′-oxindole] revealed that several compounds showed moderate cytotoxicity to SW116 cells. 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).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Product Details of 774-47-0

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

Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air was written by Wang, Qing-Dong;Zhou, Bin;Yang, Jin-Ming;Fang, Dong;Ren, Jiangmeng;Zeng, Bu-Bing. And the article was included in Synlett in 2017.Recommanded Product: 4769-96-4 This article mentions the following:

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles such as 2-phenyl-1H-indole, 6-fluoro-1H-indole, 1-methyl-1H-indole, etc. was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles such as 2-phenyl-1H-indole-3-carbaldehyde, 6-fluoro-1H-indole-3-carbaldehyde, 1-methyl-1H-indole-3-carbaldehyde, etc. in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 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

Synthesis, characterization and anticancer activity of certain 3-{4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenylimino}indolin-2-one derivatives was written by Gudipati, Rajyalakshmi;Anreddy, Rama Narsimha Reddy;Manda, Sarangapani. And the article was included in Saudi Pharmaceutical Journal in 2011.Recommanded Product: 112656-95-8 This article mentions the following:

Series of 5- or 7-substituted 3-{4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenylimino}-indolin-2-one derivatives were synthesized by treating 5-(4-aminophenyl)-1,3,4-oxadiazole-2-thiol with different isatin derivatives The newly synthesized compounds were characterized on the basis of spectral (FT-IR, ¹H NMR, MS) analyses. All the synthesized derivatives were screened for anticancer activity against HeLa cancer cell lines using MTT assay. All the synthetic compounds produced a dose dependent inhibition of growth of the cells. The IC₅₀ values of all the synthetic test compounds were found between 10.64 and 33.62 μM. The potency (IC₅₀ values) of anticancer activity of the the halo-substituted compounds was comparable with that of known anticancer agent, Cisplatin. Among the synthesized 2-indolinones, these halo-substituted compounds with halogen atom (electron withdrawing groups) at C5 position showed the most potent activity. These results indicate that C5 substituted derivatives may be useful leads for anticancer drug development in the future. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Recommanded Product: 112656-95-8).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Recommanded Product: 112656-95-8

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