M.W=150-200 | - Page 4 of 152 - Indole Building Blocks

Knepper, Kerstin’s team published research in Organic Letters in 5 | CAS: 57663-18-0

Organic Letters published new progress about 57663-18-0. 57663-18-0 belongs to indole-building-block, auxiliary class Indole,Ester, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Safety of Methyl 2-methyl-1H-indole-5-carboxylate.

Knepper, Kerstin published the artcileBartoli Indole Synthesis on Solid Supports, Safety of Methyl 2-methyl-1H-indole-5-carboxylate, the publication is Organic Letters (2003), 5(16), 2829-2832, database is CAplus and MEDLINE.

Bartoli indole synthesis was performed on solid supports. Starting from Merrifield resin, immobilization of five nitrobenzoic acids was performed. Addition of four different alkenyl Grignard reagents and basic cleavage leads to substituted Me indolecarboxylates in excellent purities. Features of this reaction are the stability of halide groups, ester moieties, and tolerance of o,o’-unsubstituted nitro resins. Heck and Sonogashira reactions are also possible with immobilized indoles.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Ivanova, Olga A.’s team published research in Chemistry – A European Journal in 22 | CAS: 220943-23-7

Chemistry – A European Journal published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, Formula: C9H6FNO.

Ivanova, Olga A. published the artcileA Straightforward Approach to Tetrahydroindolo[3,2-b]carbazoles and 1-Indolyltetrahydrocarbazoles through [3+3] Cyclodimerization of Indole-Derived Cyclopropanes, Formula: C9H6FNO, the publication is Chemistry – A European Journal (2016), 22(4), 1223-1227, database is CAplus and MEDLINE.

A rapid new approach to produce biol. relevant bisindoles, namely indolyltetrahydrocarbazoles and indolo[3,2-b]carbazoles, was developed, based on the Ga(OTf)₃-catalyzed [3+3] cyclodimerization of indole-derived donor-acceptor cyclopropanes. Chemoselectivity of the process depends on the location of the three-membered ring at the indole core.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Ambrogio, Ilaria’s team published research in Tetrahedron in 65 | CAS: 57663-18-0

Tetrahedron published new progress about 57663-18-0. 57663-18-0 belongs to indole-building-block, auxiliary class Indole,Ester, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, SDS of cas: 57663-18-0.

Ambrogio, Ilaria published the artcile3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles, SDS of cas: 57663-18-0, the publication is Tetrahedron (2009), 65(44), 8916-8929, database is CAplus.

3-(O-Trifluoroacetamidoaryl)-1-propargylic esters have been used as common synthetic intermediates for the preparation of a variety of 3-unsubstituted 2-substituted indoles. Treating Et 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates unsubstituted or containing an aryl substituent at the propargylic carbon with piperazines and Pd(PPh₃)₄ in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields of 2-aminomethylindoles are also obtained with other secondary amines. Et 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates bearing an alkyl substituent at the propargylic carbon and Et 3-(o-trifluoroacetamidoaryl)-1-propargylic acetates disubstituted at the propargylic carbon give 2-vinylic indoles with the Pd(OAc)₂/PPh₃ combination and Et₃N in THF at 80 °C. Formation of 2-vinylic indoles is quite stereoselective, generating trans vinylic derivatives, at least with the substrates that we have investigated. In the presence of formic acid, Et₃N, and Pd(PPh₃)₄ in MeCN at 80 °C, Et 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates afford 2-alkylindoles in good to excellent yields.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Narayana, B.’s team published research in Organic Chemistry: An Indian Journal in 2 | CAS: 220943-23-7

Organic Chemistry: An Indian Journal published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, Quality Control of 220943-23-7.

Narayana, B. published the artcileSimple syntheses of 5-fluoro/ chloro/ bromoindole-2-methanols and 5-fluoro/ chloro/ bromoindole-2-aldehydes, Quality Control of 220943-23-7, the publication is Organic Chemistry: An Indian Journal (2006), 2(1-3), 5-9, database is CAplus.

Efficient and simple methods for the syntheses of 5-haloindole-2-methanols and 5-haloindole-2-aldehydes have been described. 5-Haloindole-2-methanols were prepared by reduction of Me 5-haloindole-2-carboxylates with sodium borohydride in methanol/ THF media and 5-haloindole-2-aldehydes were prepared from the prepared 5-haloindole-2-methanols by oxidation with pyridinium chlorochromate or chromium trioxide-pyridine prepared in situ. The synthesized compounds were isolated in good yields and characterized by ¹H NMR, ¹³C NMR, FABMS and elemental anal.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Biswas, Subhasish’s team published research in European Journal of Organic Chemistry in 2012 | CAS: 220943-23-7

European Journal of Organic Chemistry published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, Recommanded Product: 5-Fluoro-1H-indole-2-carbaldehyde.

Biswas, Subhasish published the artcileOne-Step Synthesis of 2-Amino-5H-pyrimido[5,4-b]indoles, Substituted 2-(1,3,5-triazin-2-yl)-1H-indoles, and 1,3,5-Triazines from Aldehydes, Recommanded Product: 5-Fluoro-1H-indole-2-carbaldehyde, the publication is European Journal of Organic Chemistry (2012), 2012(18), 3492-3499, S3492/1-S3492/20, database is CAplus.

An efficient one-step synthesis of 2-amino-5H-pyrimido[5,4-b]indoles through a copper-catalyzed cascade reaction between 3-haloindole-2-carbaldehydes and guanidine hydrochloride is described. In contrast, the base-mediated reactions of either 3-haloindole-2-carbaldehydes or substituted indole-2-carbaldehydes with substituted amidine hydrochlorides in DMSO result in the formation of 2-(1,3,5-triazin-2-yl)-1H-indole derivatives in one step in excellent yields. Studies toward exploring the utility of the method demonstrate that even substituted benzaldehydes undergo a similar reaction to efficiently yield 2,4,6-trisubstituted 1,3,5-triazines. A plausible mechanism for the formation of substituted 1,3,5-triazines identifies the role of DMSO as an oxidant during the reaction.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bowroju, Suresh Kuarm’s team published research in RSC Advances in 11 | CAS: 220943-23-7

RSC Advances published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, HPLC of Formula: 220943-23-7.

Bowroju, Suresh Kuarm published the artcileI₂/DMSO-catalyzed one-pot approach for the synthesis of 1,3,4-selenadiazoles, HPLC of Formula: 220943-23-7, the publication is RSC Advances (2021), 11(10), 5724-5728, database is CAplus and MEDLINE.

A three-component cascade reaction for the synthesis of 1,3,4-selenadiazoles and their derivatives from arylaldehydes, hydrazine, and elemental selenium by using mol. iodine wais reported. This strategy was operationally simple, well-suited to a wide range of functional groups, and provided the desired products in moderate to excellent yields. The proposed mechanism predicted that the reaction tolerated a radical process.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Jang, Ye Jin’s team published research in Antiviral Research in 107 | CAS: 220943-23-7

Antiviral Research published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, Application In Synthesis of 220943-23-7.

Jang, Ye Jin published the artcileSynthesis and anti-influenza virus activity of 4-oxo- or thioxo-4,5-dihydrofuro[3,4-c]pyridin-3(1H)-ones, Application In Synthesis of 220943-23-7, the publication is Antiviral Research (2014), 66-75, database is CAplus and MEDLINE.

A series of dihydrofuropyridinones I (X = O, S; R¹ = H, Me; R² = Me, Ph; R³ = 5-fluoro-3-indolyl, 2-thienyl, 3-furyl, 3-benzothienyl, etc.) has been synthesized under conventional thermal and microwave irradiation conditions. To investigate the structure-activity relationships, two dozens of the hit analogs were synthesized. One of the hit compounds, I (X = S; R¹ = H; R² = Me; R³ = 5-fluoro-3-indolyl), had half-maximal effective concentrations of 17.4-21.1 μM against influenza A/H1N1, A/H3N2 and B viruses without any cellular toxicity at 900 μM. Among the products, I (X = S; R¹ = H; R² = Me; R³ = 2-benzothienyl, 3-thienyl, 2-thienyl, 5-Me-2-thienyl) and I (X = S; R¹ = R² = Me; R³ = 3-Me-2-thienyl) had anti-influenza viral activity comparable or superior to that of the initial hit. Based on a mode-of-action study, these compounds did not affect virus entry or RNA replication. Instead, they suppressed viral neuraminidase activity. This study is the first to demonstrate that dihydrofuropyridinones could serve as lead compounds for the discovery of alternative influenza virus inhibitors.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bakke, Jan’s team published research in Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry in 1974 | CAS: 41910-64-9

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry published new progress about Cyclization. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, SDS of cas: 41910-64-9.

Bakke, Jan published the artcileNew syntheses of substituted indoles, SDS of cas: 41910-64-9, the main research area is indole chloro phenyl; phenethyl chloride nitro cyclization; cyclization nitrophenethyl chloride.

The indoles I (R = H, 4-Cl, 6-Cl, 4-NH2) were prepd by cyclizing RC6H3(CH2CH2Cl)(NO2)-1,2 (R = H, 6-Cl, 4-Cl, 6-O2N) with Fe and dehydration of the resulting dehydroindole with Pd/C. o-O2NC6H4Me was condensed with PhCHO to give o-O2NC6H4CH2(O)HPh which was oxidized with concentrated HNO3 and the product cyclized by catalytic reduction to give 2-phenylindole.

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

McDonald, Brian G.’s team published research in Journal of the Chemical Society, Perkin Transactions 18: Organic and Bio-Organic Chemistry in 1975 | CAS: 57663-18-0

Journal of the Chemical Society, Perkin Transactions 18: Organic and Bio-Organic Chemistry published new progress about Cyclization. 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Formula: C11H11NO2.

McDonald, Brian G. published the artcileConversion of (2-chlorallyl)amines into heterocyclic compounds. I. 2-Methylindoles, 1,5,6,7-tetrahydro-3-methylindol-4-ones, and related heterocycles, Formula: C11H11NO2, the main research area is cyclization aniline chloroallyl 231; indole methyl; oxazoloquinoline; imidazopyridine; pyrroloquinoline.

The allylanilines I [R = H, Me, (CH2)2CO2Me, R1 = H; R = H, R1 = 2-Ph, 2-CO2Me, 3-Me, 4-Cl, 4-Me, 4-CO2Me], prepared by condensation of R1C6H4NHR with CH2:CClCH2R2 (R2 = Cl, I), gave 5-75% II on heating with polyphosphoric acid at 100° or BF3-MeOH at 150°. This method was used for the preparation of other heterocyclic compounds e.g. condensation of 4,7-dichloroquinoline with R3NHCH2CCl:CH2 (R3 = Ph, Et) and cyclization of the product formed gave 30-42% pyrroloquinolines III.

Baader, Manuel’s team published research in British Journal of Pharmacology in 2018 | CAS: 5654-92-2

British Journal of Pharmacology published new progress about Apoptosis. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine.

Baader, Manuel published the artcileCharacterization of the properties of a selective, orally bioavailable autotaxin inhibitor in preclinical models of advanced stages of liver fibrosis, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is autotaxin inhibitor bioavailability pharmacokinetics hepatitis liver fibrosis.

Autotaxin (ATX) is a secreted phospholipase which hydrolyzes lysophosphatidylcholine to generate lysophosphatidic acid (LPA). The extracellular signalling mol. LPA exerts its biol. actions through activation of six GPCRs expressed in various cell types including fibroblasts. Multiple preclin. studies using knockout animals, LPA receptor antagonists or ATX inhibitors have provided evidence for a potential role of the ATX/LPA axis in tissue fibrosis. Despite growing evidence for a correlation between ATX levels and the degree of fibrosis in chronic liver diseases, including viral hepatitis and hepatocellular carcinoma, the role of ATX in non-alc. steatohepatitis (NASH) remains unclear. The relevance of ATX in the pathogenesis of liver fibrosis was investigated by oral administration of Ex_31, a selective ATX inhibitor, in a 10 wk model of carbon tetrachloride-induced liver injury and in a 14 wk model of choline-deficient amino acid-defined diet-induced liver injury in rats. Oral administration of Ex_31, a selective ATX inhibitor, at 15 mg·kg-1 twice daily in therapeutic intervention mode resulted in efficient ATX inhibition and more than 95% reduction in plasma LPA levels in both studies. Treatment with Ex_31 had no effect on biomarkers of liver function, inflammation, or fibrosis and did not result in histol. improvements in diseased animals. Our findings question the role of ATX in the pathogenesis of hepatic fibrosis and the potential of small mol. ATX inhibitors for the treatment of patients with NASH and advanced stages of liver fibrosis.