Month: November 2022

Pellicciari, Roberto published the artcileOn the way to selective PARP-2 inhibitors. Design, synthesis, and preliminary evaluation of a series of isoquinolinone derivatives, Safety of 4-Hydroxy-2,3-dihydroisoindol-1-one, the main research area is excitotoxins cell death PARP2 inhibitor isoquinoline derivative SAR preparation.

PARP-1 and PARP-2 are members of the family of poly(ADP-ribose)polymerases, which are involved in the maintenance of genomic integrity under conditions of genotoxic stimuli. The different roles of the two isoforms under pathophysiol. conditions have not yet been fully clarified, and this is partially due to the lack of selective inhibitors. We report herein the synthesis and preliminary pharmacol. evaluation of a large series of isoquinolinone derivatives as PARP-1/PARP-2 inhibitors. Among them, we identified the 5-benzoyloxyisoquinolin-1(2H)-one derivative as the most selective PARP-2 inhibitor reported so far, with a PARP-2/PARP-1 selectivity index greater than 60.

ChemMedChem published new progress about Cell death. 366453-21-6 belongs to class indole-building-block, name is 4-Hydroxy-2,3-dihydroisoindol-1-one, and the molecular formula is C8H7NO2, Safety of 4-Hydroxy-2,3-dihydroisoindol-1-one.

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

Bien, Jeffrey published the artcileThe First Kilogram Synthesis of Beclabuvir, an HCV NS5B Polymerase Inhibitor, Recommanded Product: 3-Cyclohexyl-1H-indole-6-carboxylic acid, the main research area is beclabuvir diastereoselective enantioselective kilogram scale preparation; stereoselective rhodium catalyzed cyclopropanation alkylation key step preparation beclabuvir; palladium catalyzed intramol arylation key step preparation beclabuvir.

A process for the multikilogram-scale preparation of the hepatitis B NS5B RNA polymerase inhibitor beclabuvir I was developed using a diastereoselective and enantioselective cyclopropanation using the Davies catalyst Rh2(S-DOSP)4, an alkylation to merge indole and cyclopropane fragments, and an intramol. palladium-catalyzed arylation as the key steps. I·HCl was prepared in 12 linear steps with 5 isolations in an overall yield of 8%.

Organic Process Research & Development published new progress about Alkylation. 494799-17-6 belongs to class indole-building-block, name is 3-Cyclohexyl-1H-indole-6-carboxylic acid, and the molecular formula is C15H17NO2, Recommanded Product: 3-Cyclohexyl-1H-indole-6-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

Dutt, Rohit published the artcileImproved superaugmented eccentric connectivity indices – Part II: Application in development of models for prediction of hiCE and hCE1 inhibitory activities of isatins, Category: indole-building-block, the main research area is carboxylesterase liver intestine superaugmented eccentric connectivity topochem index.

Topochem. versions of all the four superaugmented eccentric connectivity indexes (denoted by: SAcξ4c, SAcξ5c, SAcξ6c, and SAcξ7c) were utilized for the development of models for prediction of hiCE and hCE1 inhibitory activities. The values of these topochem. indexes were computed for each of the 65 analogs constituting the data set using an inhouse computer program. Resulting data was analyzed and suitable models were developed after identification of the active ranges by maximization of moving average with regard to active derivatives Subsequently, two biol. activities were assigned to each analog using proposed models, which were then compared with the reported hiCE and hCE1 inhibitory activities. Statistical significance of topol. indexes/models was investigated through sensitivity, specificity, and Matthews correlation coefficient (MCC). The overall accuracy of prediction varied from a min. of 81% for a model based upon SAcξ4c to a maximum of 92% in case of a model based upon SAcξ5c with regard to hiCE inhibitory activity and from a min. of 85% for a model based upon SAcξ4c to a maximum of 94% in case of a model based upon SAcξ7c with regard to hCE1 inhibitory activity. An excellent relationship between new generation superaugmented eccentric connectivity topochem. indexes (SAcξ4c, SAcξ5c, SAcξ6c, and SAcξ7c) and hiCE and hCE1 inhibitory activities can be attributed to the sensitivity of the proposed topol. indexes toward nature, number, and relative position of heteroatom. High predictability amalgamated with high potency of the active ranges offer proposed models a vast potential for providing lead structures for development of potent and selective hiCE and hCE1 inhibitors.

Medicinal Chemistry Research published new progress about Drug design. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, 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

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.

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.

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

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.

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.

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

Ito, Yoshihiko published the artcileIndole syntheses with o-tolyl isocyanide. 3-Acylindoles and 2-substituted indoles, Safety of 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is indole acyl; tolyl isocyanide acylation; cyclization acylmethylphenyl isocyanide.

o-(Lithiomethyl)phenyl isocyanide, generated from o-tolyl isocyanide and (Me2CH)2NLi in diglyme, reacts with allyl esters to produce o-(acylmethyl)phenyl isocyanides. Similarly, acylation of 4-chloro-2-methylphenyl isocyanide, 2,4-dimethylphenyl isocyanide, and 2,6-dimethylphenyl isocyanide produces the corresponding o-(acylmethyl)phenyl isocyanides in moderate yields. o-(Acylmethyl)phenyl isocyanides are heated with Cu2O catalyst in benzene to give 3-acylindole. o-(Acylmethyl)phenyl isocyanides are hydrolyzed to afford 2-alkyl(or 2-aryl)indoles.

Journal of Organic Chemistry published new progress about Cyclization. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Safety of 2-(tert-Butyl)-5-chloro-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

Lu, Dong-Liang published the artcileAtroposelective Construction of Arylindoles by Chiral Phosphoric Acid-Catalyzed Cross-Coupling of Indoles and Quinones, Application of 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is arylindole atroposelective synthesis phosphoric acid catalyzed coupling indole quinone.

Structurally novel atropisomeric arylindole frameworks have been successfully constructed through chiral phosphoric acid-catalyzed asym. cross-coupling of indoles and quinone derivatives in a precise regioselective manner. This approach features high convergence and functional group tolerance to efficiently deliver diverse heteroaryl atropisomers with excellent enantiocontrol. The dominant formation of axial chirality but not central chirality, as the major unmet challenge for this type of reactions, was conquered by the rational and accurate modulation of the electronic and steric effects on both coupling partners. Preliminary investigation demonstrated the practicality of such axially chiral arylindoles as chiral ligands in asym. catalysis.

Organic Letters published new progress about Atropisomers. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Application of 2-(tert-Butyl)-5-chloro-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

Smith, Keith published the artcileCarbonylation of various organolithium reagents. A novel approach to heterocycles via intramolecular trapping of aromatic acyllithiums, Related Products of indole-building-block, the main research area is pivaloylaniline pivaloylaminopyridine carbonylation; pivaloyltoluidine carbonylation; cyclization carbonylation pivaloylaniline pivaloylaminopyridine; indole preparation cyclization carbonylation pivaloylaniline pivaloylaminopyridine.

Doubly lithiated N-pivaloylanilines react smoothly with carbon monoxide at 0 °C to give 3-tert-butyl-3-hydroxy-2,3-dihydro-2-indolones in good yields. Similarly, carbonylation of doubly lithiated 4-pivaloylamino- and 2-pivaloylaminopyridines at 0 °C affords the corresponding 5-aza- and 7-aza-3-tert-butyl-3-hydroxy-2,3-dihydro-2-indolones, resp., in good yields. However, carbonylation of doubly lithiated N-pivaloyl-o-toluidines takes a different course due to direct intramol. cyclization of the dilithio reagents to afford 2-tert-butylindoles without uptake of carbon monoxide.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry published new progress about Carbonylation. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Related Products of 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

Onyeibor, Onyeka published the artcileSynthesis of Some Cryptolepine Analogues, Assessment of Their Antimalarial and Cytotoxic Activities, and Consideration of Their Antimalarial Mode of Action, Safety of 4,5-Dichloroisatin, the main research area is cryptolepine analog preparation; antiplasmodial cytotoxic antimalarial cryptolepine analog preparation; beta hematin formation inhibition cryptolepine preparation.

A series of analogs of cryptolepine were synthesized and evaluated for their in vitro antiplasmodial and cytotoxic properties. The IC50 values of several compounds against Plasmodium falciparum (strain K1) were <0.1 μM, 5-10-fold lower than that of cryptolepine but their cytotoxicities were only 2-4 times greater than that of cryptolepine. Compounds with a halogen in the quinoline ring and a halogen or a nitro group in the indole ring have enhanced antiplasmodial activity. In mice infected with P. berghei, the 7-bromo-2-chloro and 2-bromo-7-nitro derivatives of cryptolepine suppressed parasitemia by >90% at doses of 25 mg kg-1 day-1 with no apparent toxicity to the mice. 2,7-Dibromocryptolepine was evaluated at several dose levels, and a dose-dependent suppression of parasitemia was seen (ED90 = 21.6 mg kg-1 day-1). The antimalarial mode of action of cryptolepine suppressed parasitemia by >90% at doses of 25 mg kg-1 day-1 with no apparent toxicity to the mice. appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation. A number of analogs were assessed for their effects on the inhibition of β-hematin (hemozoin) formation, and the results were compared with their antiplasmodial activities having taken account of their predicted accumulation into the acidic parasite food vacuole. No correlation was seen (r2 = 0.0781) suggesting that the potent antimalarial activity of compounds such as 2,7-dibromocryptolepine involves other mechanisms in addition to the inhibition of hemozoin formation.

Journal of Medicinal Chemistry published new progress about Antimalarials. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, Safety of 4,5-Dichloroisatin.

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

Yang, Guoqiang published the artcilePd(II)-Catalyzed meta-C-H Olefination, Arylation, and Acetoxylation of Indolines Using a U-Shaped Template, Formula: C8H8ClN, the main research area is regioselective meta carbon hydrogen bond olefination indoline palladium catalyst; acetoxylation indoline palladium catalyst; arylation indoline palladium catalyst.

Meta-C-H olefination, arylation, and acetoxylation of indolines have been developed using nitrile-containing templates. The combination of a monoprotected amino acid ligand and the nitrile template attached at the indolinyl nitrogen via a sulfonamide linkage is crucial for the meta-selective C-H functionalization of electron-rich indolines that are otherwise highly reactive toward electrophilic palladation at the para-positions. A wide range of synthetically important and advanced indoline analogs are selectively functionalized at the meta-positions.

Journal of the American Chemical Society published new progress about Acetoxylation. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Formula: C8H8ClN.

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