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

Wang, Xiaomin et al. published their research in Applied Microbiology and Biotechnology in 2014 | CAS: 1016-47-3

N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3) 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 of 1016-47-3

A PKS I gene-based screening approach for the discovery of a new polyketide from Penicillium citrinum Salicorn 46 was written by Wang, Xiaomin;Wang, Hui;Liu, Tianxing;Xin, Zhihong. And the article was included in Applied Microbiology and Biotechnology in 2014.Application of 1016-47-3 This article mentions the following:

Salicorn 46, an endophytic fungus isolated from Salicornia herbacea Torr., was identified as Penicillium citrinum based on its internal transcribed spacer and ribosomal large-subunit DNA sequences using a type I polyketide synthase (PKS I) gene screening approach. A new polyketide, penicitriketo (I), and seven known compounds, including ergone (2), (3β,5α,8α,22E)-5,8-epidioxyergosta-6,9,22-trien-3-ol (3), (3β,5α,8α,22E)-5,8-epidioxyergosta-6,22-dien-3-ol (4), stigmasta-7,22-diene-3β,5α,6α-triol (5), 3β,5α-dihydroxy-(22E,24R)-ergosta-7,22-dien-6β-yl oleate (6), N_b-acetyltryptamine (7), and 2-(1-oxo-2-hydroxyethyl) furan (8), were isolated from the culture of Salicorn 46, and their chem. structures were elucidated by spectroscopic anal. Antioxidant experiments revealed that compound I possessed moderate DPPH radical scavenging activity with an IC₅₀ value of 85.33 ± 1.61 μM. Antimicrobial assays revealed that compound 2 exhibited broad-spectrum antimicrobial activity against Candida albicans, Clostridium perfringens, Mycobacterium smegmatis, and Mycobacterium phlei with minimal inhibitory concentration (MIC) values of 25.5, 25.5, 18.5, and 51.0 μM, resp. Compound 3 displayed potent antimicrobial activities against C. perfringens and Micrococcus tetragenus with a MIC value of 23.5 μM. Compounds 5 and 6 showed high levels of selectivity toward Bacillus subtilis and M. phlei with MIC values of 22.5 and 14.4 μM, resp. The results of this study highlight the use of PCR-based techniques for the screening of new polyketides from endophytic fungi containing PKS I genes. In the experiment, the researchers used many compounds, for example, N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3Application of 1016-47-3).

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

Rojas-Fernandez, Carlos et al. published their research in Drugs & Aging in 2014 | CAS: 115956-12-2

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, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. 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). Synthetic Route of C19H20N2O3

Current Use of Domperidone and Co-prescribing of Medications that Increase Its Arrhythmogenic Potential Among Older Adults: A Population-Based Cohort Study in Ontario, Canada was written by Rojas-Fernandez, Carlos;Stephenson, Anne L.;Fischer, Hadas D.;Wang, Xuesong;Mestre, Tiago;Hutson, Janine R.;Pondal, Margarita;Lee, Douglas S.;Rochon, Paula A.;Marras, Connie. And the article was included in Drugs & Aging in 2014.Synthetic Route of C19H20N2O3 This article mentions the following:

Background and Objectives: Domperidone is commonly used to treat nausea and gastrointestinal disorders. Recent data suggests that it may increase the risk of sudden cardiac death, particularly in older people. Little is known about how it is used in contemporary practice. This study sought to characterize the population of older adults newly dispensed domperidone, describe dosages of domperidone used, and determine the frequency of co-prescribing domperidone with medications that may increase the arrhythmogenic potential of domperidone. Methods: This is a retrospective cohort study using administrative health database information from Ontario, Canada. Prescription medication records were obtained from the Ontario Drug Benefit Claims Database. Diagnostic codes were obtained from the Ontario Health Insurance Plan Database, the Canadian Institute for Health Information Discharge Abstract Database, and the same-day surgery database. Patients who received a new prescription for domperidone between Apr. 1, 2003 and March 31, 2010 were included. Results: A total of 122,233 patients met inclusion criteria; 85 % were between 66 and 84 years old and 63 % were female. The mean estimated daily domperidone dose was 35 mg, and the estimated daily dose was <40 mg for 62 % of users. Strong or moderately strong cytochrome P 450 (CYP) 3A4 inhibitors were co-prescribed for 4.3 and 10.7 % of users, while medications with a known risk or possible risk for torsades de pointes (TdP) were co-prescribed to 18.3 and 18.8 % of users. Conclusions: Older domperidone users were commonly co-prescribed drugs with the potential to increase the risk for TdP. These combinations should be avoided, as iatrogenic QT prolongation is a modifiable risk factor for TdP. 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: 115956-12-2Synthetic Route of C19H20N2O3).

Poje, Goran et al. published their research in European Journal of Medicinal Chemistry in 2022 | CAS: 442-51-3

7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole (cas: 442-51-3) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application In Synthesis of 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole

Design and synthesis of harmiquins, harmine and chloroquine hybrids as potent antiplasmodial agents was written by Poje, Goran;Pessanha de Carvalho, Lais;Held, Jana;Moita, Diana;Prudencio, Miguel;Perkovic, Ivana;Tandaric, Tana;Vianello, Robert;Rajic, Zrinka. And the article was included in European Journal of Medicinal Chemistry in 2022.Application In Synthesis of 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole This article mentions the following:

Malaria remains one of the major health problems worldwide. The lack of an effective vaccine and the increasing resistance of Plasmodium to the approved antimalarial drugs demands the development of novel antiplasmodial agents that can effectively prevent and/or treat this disease. Harmiquins represent hybrids that combine two moieties with different mechanisms of antiplasmodial activity in one mol., i.e., a chloroquine (CQ) scaffold, known to inhibit heme polymerization and a β-carboline ring capable of binding to P. falciparum heat shock protein 90 (PfHsp90). Here we present their synthesis, evaluation of biol. activity and potential mechanism of action. The synthesized hybrids differed in the type of linker employed (triazole ring or amide bond) and in the position of the substitution on the β-carboline core of harmine. The antiplasmodial activity of harmiquins was evaluated against the erythrocytic stage of the Plasmodium life cycle, and their cytotoxic effect was tested on HepG2 cells. The results showed that harmiquins exerted remarkable activity against both CQ-sensitive (Pf3D7) and CQ-resistant (PfDd2, PfK1, and Pf7G8). P. falciparum strains. The most active compound, I, displayed single-digit nanomolar IC₅₀ value against Pf3D7 (IC₅₀ = 2.0 ± 0.3 nM). Importantly, it also showed significantly higher activity than CQ against the resistant Plasmodium strains and had a very high selectivity index (4450). Harmiquins may act through the inhibition of heme polymerization and binding to the ATP binding site of the PfHsp90, which would explain their increased activity against the CQ-resistant Plasmodium strains. These results establish harmiquins as valuable antiplasmodial hits for future optimization. In the experiment, the researchers used many compounds, for example, 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole (cas: 442-51-3Application In Synthesis of 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole).

Eastwood, Paul et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2011 | CAS: 1190861-43-8

6-Bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-2-one (cas: 1190861-43-8) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Related Products of 1190861-43-8

Indolin-2-one p38α inhibitors III: Bioisosteric amide replacement was written by Eastwood, Paul;Gonzalez, Jacob;Gomez, Elena;Caturla, Francisco;Aguilar, Nuria;Mir, Marta;Aiguade, Josep;Matassa, Victor;Balague, Cristina;Orellana, Adelina;Dominguez, Maria. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Related Products of 1190861-43-8 This article mentions the following:

Crystallog. structural information was used in the design and synthesis of a number of bioisosteric derivatives to replace the amide moiety in a lead series of p38α inhibitors which showed general hydrolytic instability in human liver preparations Triazole derivative I was found to have moderate bioavailability in the rat and demonstrated potent in-vivo activity in an acute model of inflammation. In the experiment, the researchers used many compounds, for example, 6-Bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-2-one (cas: 1190861-43-8Related Products of 1190861-43-8).

Baraboy, V. A. et al. published their research in Dopovidi Akademii Nauk Ukraini in 1994 | 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. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure.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 38101-59-6

Antiradiation effect of low-molecular thymic factors on the blood system was written by Baraboy, V. A.;Yalkut, S. I.;Savtsova, Z. D.;Zhukova, V. M.;Zaritskaya, M. Yu.. And the article was included in Dopovidi Akademii Nauk Ukraini in 1994.Product Details of 38101-59-6 This article mentions the following:

The therapeutic antiradiation effect of the thymic factors vilosen and thymogen was studied in male mice exposed to x-rays. In irradiated only mice, 50% of the animals died whereas 29.6% and 50% of the animals died that were also treated with vilosen and thymogen, resp. The effects of the thymic factors on blood corpuscles and cell number indexes of lymphoid organs were also studied. 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: 38101-59-6Product Details of 38101-59-6).

Zhang, Lingjuan et al. published their research in Applied Catalysis, B: Environmental in 2023 | CAS: 56341-41-4

5-Fluoroindolin-2-one (cas: 56341-41-4) 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.Computed Properties of C8H6FNO

Tuning band structures of Hf-PCN-224(M) for β-Carbonyl C(sp³)-H bond activation and difunctionalization: Tandem C(sp³) radical cross-coupling through photoredox was written by Zhang, Lingjuan;Ma, Lijuan;Yuan, Jincong;Zhang, Xian-Ming;Tang, Zhiyong. And the article was included in Applied Catalysis, B: Environmental in 2023.Computed Properties of C8H6FNO This article mentions the following:

The construction of C(sp³)-C(sp³) bonds by different C(sp³) radicals coupling reactions is still unexplored due to the high bond dissociation energy of C(sp³)-H bond and the difficulty for selective generating of C(sp³) radical. Benefiting from the precisely regulating for band structures of Hf-PCN-224(M), the β-carbonyl C(sp³)-H bonds are effectively oxidized by photo-generated holes to affording C(sp³) radicals in this work. C(sp³)-C(sp³) and C(sp³)-O bonds are constructed by tandem radical-radical cross-coupling, hydrogen atom transfer (HAT), and radical-radical cross-coupling between two C(sp³)-H bonds, enabling an effective C3-difunctionalization of indolin-2-ones under photo-thermo synergetic catalysis on Hf-PCN-224(Cu). Significantly, OH serves as triple roles, introduced hydroxyl group in situ, HAT abstractor and α-heteroatom for secondary activating C(sp³)-H bonds. Control experiments, EPR spectroscopy and DFT calculation provide insight into the tandem radicals cross-coupling mechanism. This operable strategy opens up a door for the difunctionalization of C(sp³)-H bonds in heterogeneous photoredox manner. In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Computed Properties of C8H6FNO).

Yu, Zhi-yin et al. published their research in Tianran Chanwu Yanjiu Yu Kaifa in 2015 | CAS: 1016-47-3

N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3) 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). Recommanded Product: N-(2-(1H-Indol-3-yl)ethyl)acetamide

Isolation, identification and antimicrobial activity of secondary metabolites from a soil-derived Streptomyces from arid habitats of Qinghai was written by Yu, Zhi-yin;Yu, Ming-ming;Luo, Jian-ying;Su, Can;Xue, Quan-hong;Huang, Sheng-xiong;Sun, Yun;Ma, Ya-tuan. And the article was included in Tianran Chanwu Yanjiu Yu Kaifa in 2015.Recommanded Product: N-(2-(1H-Indol-3-yl)ethyl)acetamide This article mentions the following:

Five compounds, including N-acetyltyramine(1), N-acetyltryptamine(2), pyrrole-2-carboxamide(3), inthomycin C(4) and inthomycin B(5), were isolated from the fermentation broth of Streptomyces pactum KIB-HL8, and their structures were elucidated by anal. of NMR and MS data. In addition, compound 4 moderately inhibited growth of Staphylococcus aureus. Compounds 1 and 2 showed significant antifungal activity against Botrytis cinerea. Compound 3 displayed inhibitory activity against Alternaria solani. In the experiment, the researchers used many compounds, for example, N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3Recommanded Product: N-(2-(1H-Indol-3-yl)ethyl)acetamide).

Pan, Ling et al. published their research in Advanced Synthesis & Catalysis in 2021 | CAS: 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.HPLC of Formula: 1076-74-0

Cyclization of Vinylketene Dithioacetals: A Synthetic Strategy for Substituted Thiophenes was written by Pan, Ling;Zheng, Baihui;Yang, Xiaohui;Deng, Liping;Li, Yifei;Liu, Qun. And the article was included in Advanced Synthesis & Catalysis in 2021.HPLC of Formula: 1076-74-0 This article mentions the following:

A synthetic strategy for the synthesis of substituted thiophenes is described by the one-pot reaction of indoles with ketene dithioacetals under mild reaction conditions. Promoted by triflic acid (TfOH), the reaction of indoles with the easily available α-acetyl ketene dithioacetals resulted in the formation of vinylketene dithioacetals via condensation instead of the well known nucleophilic addition-alkylthio elimination process. In the presence of CuBr₂, vinylketene dithioacetals can cyclize into the corresponding substituted thiophenes. This transformation may benefit from the acidic reaction conditions and the steric effects of the 2-substituted indoles. In the experiment, the researchers used many compounds, for example, 5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0HPLC of Formula: 1076-74-0).

Li, Shichen et al. published their research in Synthesis in 2022 | CAS: 83-34-1

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

A Direct Method for Synthesis of Fluorinated Quinazolinones and Quinoxalines Using Fluorinated Acids without Metals or Additives was written by Li, Shichen;Lv, Xueyan;Ren, Jianing;Feng, Lei;Ma, Chen. And the article was included in Synthesis in 2022.Name: 3-Methyl-1H-indole This article mentions the following:

A direct method using trifluoroacetic acid as a CF₃ source for the synthesis of 2-(trifluoromethyl)quinazolin-4-ones and 4-(trifluoromethyl)pyrrolo/indolo[1,2- a]quinoxalines without any catalysts or additives was reported; a wide range of fluorinated compounds were obtained in 52%-94% yield. In the experiment, the researchers used many compounds, for example, 3-Methyl-1H-indole (cas: 83-34-1Name: 3-Methyl-1H-indole).

Jiang, B. et al. published their research in Tetrahedron Letters in 2001 | CAS: 149108-61-2

(1-tosyl-1H-Indol-3-yl)boronic acid (cas: 149108-61-2) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Formula: C15H14BNO4S

A highly stereoselective synthesis of indolyl N-substituted glycines was written by Jiang, B.;Yang, C.-G.;Gu, X.-H.. And the article was included in Tetrahedron Letters in 2001.Formula: C15H14BNO4S This article mentions the following:

Optically active N-substituted α-indolylglycines were synthesized with high diastereoselectivity by Mannich reaction of an indolylboronic acid with glyoxylic acid using (R)-α-methylbenzylamine as the chiral auxiliary. The absolute configuration of one of the products was determined by a single-crystal x-ray anal. In the experiment, the researchers used many compounds, for example, (1-tosyl-1H-Indol-3-yl)boronic acid (cas: 149108-61-2Formula: C15H14BNO4S).