Month: November 2022

Saczewski, Franciszek published the artcile1-[(Imidazolin-2-yl)amino]indoline and 1-[(imidazolin-2-yl)amino]1,2,3,4-tetrahydroquinoline derivatives: new insights into their circulatory activities, Category: indole-building-block, the main research area is imidazolinylamino indoline hydrochloride preparation mol modeling imidazoline adrenoceptor antihypertensive; quinoline imidazolinylamino hydrochloride preparation mol modeling imidazoline adrenoceptor antihypertensive.

N-[(Imidazolinyl)amino]indoline-hydrochlorides I·HCl [R = H, 2-CH3, 7-CH3, 4-Cl] and N-[(imidazolinyl)amino]tetrahydroquinoline-hydrochlorides II·HCl [R = H, 8-CH3] were synthesized and tested in vitro for their affinities to α1 and α2-adrenoceptors as well as imidazoline I1 and I2 receptors. The compounds most potent at either α1 or α2-adrenoceptors were administered i.v. to normotensive Wistar rats to determine their effects on mean arterial blood pressure and heart rate. Upon i.v. administration at dose of 0.1 mg/kg to normotensive male Wistar rats, the initial transient pressor effect was followed by long-lasting hypotension and bradycardia. The results revealed that the synthesized compounds I and II were found to possess circulatory profile characteristic of the centrally acting clonidine-like hypotensive imidazolines.

Acta Poloniae Pharmaceutica published new progress about Adrenoceptor antagonists. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, 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

Chou, Pi-Tai published the artcileExcited-State Double Proton Transfer in 3-Formyl-7-azaindole: Role of the nπ* State in Proton-Transfer Dynamics, Category: indole-building-block, the main research area is excited state double proton transfer dynamics formylazaindole hydrogen bonding.

3-Formyl-7-azaindole (3FAI) and its derivatives have been synthesized to study the role of the nπ* state in the excited-state double proton transfer (ESDPT) reaction. In 3FAI monomer as well as its associated hydrogen-bonded complexes the lowest excited singlet state has been concluded to be in the 1nπ* configuration. The association constants incorporating the hydrogen bonding formation were determined to be 1.9 × 104 (313 K), 2.2 × 104 (298 K) and 1.8 × 105 M-1 (298 K) for 3FAI dimer, 3FAI/azacyclohexanone and 3FAI/acetic acid, resp., in cyclohexane. In alcs., the rate of solvent (e.g., methanol) diffusional migration, forming a “”correct”” precursor for ESDPT, is concluded to be much slower than the rate of Sππ* → Snπ* internal conversion which has been deduced to be 4.37 × 1012 s-1. ESDPT is prohibited in the Snπ* state of which the relaxation dynamics are dominated by the rate of Snπ* → Tππ* intersystem crossing. In contrast, for 3FAI dimer or 3FAI/acetic acid complex possessing intact dual hydrogen bonds the intrinsic ESDPT is competitive with the rate of Sππ* → Snπ* internal conversion, resulting in a prominent imine-like tautomer emission. The results provide the first model among 7-azaindole analogs in which the fast rate of Sππ* → Snπ* internal conversion serves as an internal clock to examine the mechanism of guest mols. (including the bulk alcs.) assisted ESDPT.

Journal of Physical Chemistry A published new progress about Density functional theory. 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, 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

Fuller, Janis J. published the artcileBiosynthesis of violacein, structure and function of L-tryptophan oxidase VioA from Chromobacterium violaceum, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is tryptophan oxidase Chromobacterium structure function inhibitor substrate analog preparation; crystal structure tryptophan oxidase Chromobacterium; SAXS tryptophan oxidase Chromobacterium; L-tryptophan oxidase; crystal structure; enzyme mechanism; enzyme-inhibitor complex; flavoprotein; redox chemistry; site-directed mutagenesis; substrate specificity; violacein.

Violacein is a natural purple pigment of Chromobacterium violaceum with potential medical applications as antimicrobial, antiviral, and anticancer drugs. The initial step of violacein biosynthesis is the oxidative conversion of L-tryptophan into the corresponding α-imine catalyzed by the flavoenzyme, L-tryptophan oxidase (VioA). A substrate-related (3-(1H-indol-3-yl)-2-methylpropanoic acid) and a product-related (2-(1H-indol-3-ylmethyl)prop-2-enoic acid) competitive VioA inhibitor was synthesized for subsequent kinetic and x-ray crystallog. investigations. Structures of the binary VioA·FADH2 and of the ternary VioA·FADH2·2-(1H-indol-3-ylmethyl)prop-2-enoic acid complex were resolved. VioA formed a “”loosely associated”” homodimer as indicated by SAXS experiments VioA belongs to the glutathione reductase family 2 of FAD-dependent oxidoreductases according to the structurally conserved cofactor binding domain. The substrate-binding domain of VioA was mainly responsible for the specific recognition of L-tryptophan. Other canonical amino acids were efficiently discriminated with a minor conversion of L-phenylalanine. Furthermore, 7-aza-tryptophan, 1-methyl-tryptophan, 5-methyl-tryptophan, and 5-fluoro-tryptophan were efficient substrates of VioA. The ternary product-related VioA structure indicated involvement of protein domain movement during enzyme catalysis. Extensive structure-based mutagenesis in combination with enzyme kinetics (using L-tryptophan and substrate analogs) identified Arg-64, Lys-269, and Tyr-309 as key catalytic residues of VioA. An increased enzyme activity of protein variant H163A in the presence of l-phenylalanine indicated a functional role of His-163 in substrate binding. The combined structural and mutational analyses led to a detailed understanding of VioA substrate recognition. Related strategies for the in vivo synthesis of novel violacein derivatives were discussed.

Journal of Biological Chemistry published new progress about Chromobacterium violaceum. 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.

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

Tong, Kun published the artcileVisible-Light-Induced Direct Oxidative C-H Amidation of Heteroarenes with Sulfonamides, Related Products of indole-building-block, the main research area is heterocyclic compound preparation regioselective photochem; heteroarene sulfonamide oxidative carbon hydrogen amidation iridium catalyst; C−H amidation; heterocycles; nitrogen-centered radicals; photochemistry; visible light.

A direct oxidative C-H amidation of heteroarenes, e.g., I, with sulfonamides RNHSO2R1 [R = CH3, C6H5, oxan-4-yl, etc.; R1 = CH3(CH2)4, C6H5, c-C3H5, pyridin-3-yl, etc.] via nitrogen-centered radicals has been described. Nitrogen-centered radicals are directly generated from oxidative cleavage of NH bonds under visible-light photoredox catalysis. Sulfonamides, which are easily accessed, used as tunable nitrogen sources. Bleach (aqueous NaClO solution), which is clean and economic, was used as the solely oxidant. A variety of heteroarenes, including indoles, pyrroles, and benzofurans, can undergo this amidation with high yields (up to 92%). These reactions are highly regioselective, and all the products, e.g., II, are isolated as single regioisomer.

Chemistry – A European Journal published new progress about Amidation (regioselective). 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, 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

Ranasinghe, Nadeesha published the artcileExtending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry, Safety of Methyl 6-nitro-1H-indole-2-carboxylate, the main research area is Hemetsberger Knittel indole synthesis microwave chem.

Microwave, flow and combination methodologies were applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodol. allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chem., allowing formation of peptide adducts which can be subsequently labeled with fluorine tags.

Bioorganic & Medicinal Chemistry Letters published new progress about [3+2] Cycloaddition reaction. 136818-66-1 belongs to class indole-building-block, name is Methyl 6-nitro-1H-indole-2-carboxylate, and the molecular formula is C10H8N2O4, Safety of Methyl 6-nitro-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

Liang, Taoyuan published the artcileStraightforward access to novel indolo[2,3-b]indoles via aerobic copper-catalyzed [3+2] annulation of diarylamines and indoles, HPLC of Formula: 13523-93-8, the main research area is diarylamino indoloindole chemoselective preparation; diarylamine indole aerobic annulation copper catalyst.

An unprecedented aerobic copper-catalyzed [3+2] annulation reaction of diarylamines with indoles was reported, which allowed direct access to novel 2-diarylamino-indolo[2,3-b]indoles I [R = Ph, 4-MeC6H4, 4-ClC6H4, etc.; R1 = Me, Et, Bn, etc.; R2 = H, 4-Me, 6-F, etc.; Ar = Ph, 4-MeC6H4, 4-t-BuC6H4, etc.; Ar1 = Ph, 4-MeC6H4], a class of potential photoelec. device mols. The developed transformation proceeded with broad substrate scope, good functional group tolerance, high chemo-selectivity and no need for pre-preparation of specific agents, which offered a practical route for diverse and atom-economic synthesis of the desired products.

Chemical Communications (Cambridge, United Kingdom) published new progress about [3+2] Cycloaddition reaction. 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, HPLC of Formula: 13523-93-8.

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

Lopez-Valdez, German published the artcileConvenient access to isoindolinones via carbamoyl radical cyclization: Synthesis of cichorine and 4-hydroxyisoindolin-1-one natural products, Recommanded Product: 4-Hydroxy-2,3-dihydroisoindol-1-one, the main research area is isoindolinone preparation oxidative radical cyclization; cichorine synthesis oxidative radical cyclization; hydroxyisoindolinone synthesis oxidative radical cyclization; zinnimidine formal synthesis oxidative radical cyclization.

An efficient and convenient access to 2-tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilauroyl peroxide (DLP) mediated rearomatization to generate the isoindolinone ring system. Addnl., the syntheses of cichorine and 4-hydroxyisoindolin-1-one natural products were carried out to underscore the synthetic potential of this xanthate-based carbamoyl radical-oxidative cyclization.

Tetrahedron published new progress about Radical oxidative cyclization. 366453-21-6 belongs to class indole-building-block, name is 4-Hydroxy-2,3-dihydroisoindol-1-one, and the molecular formula is C8H7NO2, Recommanded Product: 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

Duan, Yingqian published the artcileVisible-light-induced three-component 1,2-difluoroalkylarylation of styrenes with α-carbonyl difluoroalkyl bromides and indoles, Recommanded Product: 4-(Benzyloxy)-1-methyl-1H-indole, the main research area is indole difluoro preparation regioselective; styrene indole carbonyl difluoroalkyl bromide difluoroalkylarylation multicomponent photoredox catalyst.

A novel visible light photoredox catalysis three-component 1,2-difluoroalkylarylation of alkenes RCH=CH2 (R = 4-methoxyphenyl, 2-methoxyphenyl, 4-methylphenyl) and 1,2-dihydronaphthalene was disclosed, and two new C-C bonds were generated in a single step through regioselective incorporation of a CF2 group and a variety of indoles I (R1 = H, 5-MeO, 4-OBn, 6-F, etc.; R2 = Me, Bn) to C=C bonds. The well-designed photoredox system achieved the synthesis of a series of difluoro-containing indole derivatives, e.g., II with mild conditions and a broad substrate scope.

Organic Chemistry Frontiers published new progress about Fluoroalkylation (heteroaryl). 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Recommanded Product: 4-(Benzyloxy)-1-methyl-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

Damgaard, Maria published the artcileIdentification of the First Highly Subtype-Selective Inhibitor of Human GABA Transporter GAT3, COA of Formula: C8H3Cl2NO2, the main research area is isatin derivative screening structure preparation GABA transporter GAT3 inhibitor; GABA uptake; hGAT3 selective; inhibitor; isatin; kinetics; noncompetitive.

Screening a library of small-mol. compounds using a cell line expressing human GABA transporter 3 (hGAT3) in a [3H]GABA uptake assay identified isatin derivatives as a new class of hGAT3 inhibitors. A subsequent structure-activity relationship (SAR) study led to the identification of hGAT3-selective inhibitors (i.e., compounds 20 and 34) that were superior to the reference hGAT3 inhibitor, (S)-SNAP-5114, in terms of potency (low micromolar IC50 values) and selectivity (>30-fold selective for hGAT3 over hGAT1/hGAT2/hBGT1). Further pharmacol. characterization of compound 20 (5-(thiophen-2-yl)indoline-2,3-dione) revealed a noncompetitive mode of inhibition at hGAT3. This suggests that this compound class, which has no structural resemblance to GABA, has a binding site different from the substrate, GABA. This was supported by a mol. modeling study that suggested a unique binding site that matched the observed selectivity, inhibition kinetics, and SAR of the compound series. These compounds are the most potent GAT3 inhibitors reported to date that provide selectivity for GAT3 over other GABA transporter subtypes.

ACS Chemical Neuroscience published new progress about Central nervous system agents. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, COA of Formula: C8H3Cl2NO2.

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

Zhao, Fei published the artcileMonoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization, Application In Synthesis of 41910-64-9, the main research area is monoamine oxidase indole indoline photocatalytic cyclization dearomatization.

The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and exptl. results of the biotransformation. This methodol. represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.

ACS Catalysis published new progress about Biotransformation (whole-cell). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Application In Synthesis of 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