Month: November 2022

Ren, Albert published the artcileDiscovery of a lead series of potent benzodiazepine 5-HT2C receptor agonists with high selectivity in functional and binding assays, Synthetic Route of 41910-64-9, the main research area is food intake reduction 5HT2C receptor agonists lead; 5-HT(2C) receptor; Agonist; GPCR; Lead identification.

A series of potential new 5-HT2 receptor scaffolds based on a simplification of the clin. studied, 5-HT2CR agonist vabicaserin, were designed. An in vivo feeding assay early in our screening process played an instrumental part in the lead identification process, leading us to focus on a 6,5,7-tricyclic scaffold. A subsequent early SAR investigation provided potent agonists of the 5-HT2C receptor that were highly selective in both functional and binding assays, had good rat PK properties and that significantly reduced acute food intake in the rat.

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT2A receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Synthetic Route 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

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, Name: Methyl 2-methyl-1H-indole-5-carboxylate, the main research area is amino methyl indole preparation; vinyl indole preparation; alkyl indole preparation.

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.

Tetrahedron published new progress about Heterocyclic compounds, nitrogen Role: SPN (Synthetic Preparation), PREP (Preparation). 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Name: Methyl 2-methyl-1H-indole-5-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

Lamotte, Yann published the artcileSynthesis and biological activities of novel indole derivatives as potent and selective PPARγ modulators, Synthetic Route of 57663-18-0, the main research area is biphenylcarboxylic acid indolylmethyl preparation peroxisome proliferator activated receptor modulator; acid biphenylcarboxylic indolylmethyl preparation PPAR gamma modulator potency SAR; indolylmethyl biphenylcarboxylic acid preparation antidiabetic PPAR partial agonist activity.

Starting from the structure of Telmisartan, a new series of potent and selective PPARγ modulators was identified. The synthesis, in vitro and in vivo evaluation of the most potent compounds were reported and the X-ray structure of compound I bound to the PPARγ ligand binding domain was described.

Bioorganic & Medicinal Chemistry Letters published new progress about Hematocrit. 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Synthetic Route of 57663-18-0.

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

Nakamura, Hidemitsu published the artcileTriazole Ureas Covalently Bind to Strigolactone Receptor and Antagonize Strigolactone Responses, Safety of 4-Chloroindoline, the main research area is Oryza tillering triazole urea strigolactone signaling; covalent antagonist; crystal structure; strigolactone; triazole urea.

Strigolactones, a class of plant hormones with multiple functions, mediate plant-plant and plant-microorganism communications in the rhizosphere. In this study, we developed potent strigolactone antagonists, which covalently bind to the strigolactone receptor D14, by preparing an array of triazole urea compounds Using yeast two-hybrid and rice-tillering assays, we identified a triazole urea compound KK094 as a potent inhibitor of strigolactone receptors. Liquid chromatog.-tandem mass spectrometry anal. and X-ray crystallog. revealed that KK094 was hydrolyzed by D14, and that a reaction product of this degradation covalently binds to the Ser residue of the catalytic triad of D14. Furthermore, we identified two triazole urea compounds KK052 and KK073, whose effects on D14-D53/D14-SLR1 complex formation were opposite due to the absence (KK052) or presence (KK073) of a trifluoromethyl group on their Ph ring. These results demonstrate that triazole urea compounds are potentially powerful tools for agricultural application and may be useful for the elucidation of the complicated mechanism underlying strigolactone perception.

Molecular Plant published new progress about Germination. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Safety of 4-Chloroindoline.

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

Huang, Y. published the artcileSynthesis of potent and selective dopamine D4 antagonists as candidate radioligands, Computed Properties of 5654-92-2, the main research area is pyridinylpyrrolyl arylpiperazine preparation dopamine serotonin antagonist; substitution azagramine arylpiperazine.

A series of dopamine D4 antagonists, pyridinylpyrrolyl arylpiperazines I (R = F, MeO, R1 = H; R = H, R1 = F, MeO, MeS, CF3, CH:CH2, Et, Pr, Ph), was synthesized and evaluated as potential candidates for development as positron emission tomog. (PET) radioligands. Thus, azagramine II was reacted with the corresponding arylpiperazine in xylene under reflux to give I in 45 to 82% yield. All new compounds display high affinity and selectivity for the D4 receptors and compounds I (R = H, R1 = MeO; R = MeO, R1 = H; R = H, R1 = MeS) were identified as candidates for radioligand development. The activity against serotonin receptors was also examined

Bioorganic & Medicinal Chemistry Letters published new progress about Dopamine D4 receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (antagonists). 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, Computed Properties of 5654-92-2.

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

Bromidge, Steven M. published the artcileNovel and Selective 5-HT2C/2B Receptor Antagonists as Potential Anxiolytic Agents: Synthesis, Quantitative Structure-Activity Relationships, and Molecular Modeling of Substituted 1-(3-Pyridylcarbamoyl)indolines, Synthetic Route of 1677-47-0, the main research area is pyridylcarbamoylindoline preparation 5HT receptor antagonist anxiolytic.

The synthesis, biol. activity, and mol. modeling of a novel series of substituted 1-(3-pyridylcarbamoyl)indolines are reported. These compounds are isosteres of the previously published indole urea SB-206553 and illustrate the use of aromatic disubstitution as a replacement for fused five-membered rings in the context of 5-HT2C/2B receptor antagonists. By targeting a region of space previously identified as sterically allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor, a number of compounds which are the most potent and selective 5-HT2C/2B receptor antagonists yet reported, were identified. 1-(3-Pyridylcarbamoyl)-5-methylthio-6-trifluoromethylindoline was selected on the basis of its overall biol. profile for further evaluation as a novel, potential nonsedating anxiolytic agent. A CoMFA anal. of these compounds produced a model with good predictive value and in addition good qual. agreement with both a 5-HT2C receptor model and a proposed binding mode for this class of ligands within that model.

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

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

Pierce, Larry T. published the artcileSynthesis of novel 3,4-diaryl-5-aminopyrazoles as potential kinase inhibitors, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is aryl aminopyrazole preparation potential kinase inhibitor.

Synthesis of a diverse series of novel 3,4-diaryl-5-aminopyrazoles as candidates in the development of new protein kinase inhibitors is reported for the first time. In the course of a wider study into bisindolylmaleimide (BIM) derivatives, we examined a novel 5-aminopyrazole heterocyclic moiety as a structural analog of the highly potent VEGF-R2/3 inhibitor pyrrole-2-one, I. The versatile nature of this pharmacophore allows considerable scope for derivatization and hence exploration of structure activity relationships. Consequently, a variety of structural modifications were used in order to diversify the aminopyrazole ring substituents. Bicyclic derivatives of the parent aminopyrazoles, II (X=CH, X=N), were also synthesized as a means of probing the kinase active site, leading to formation of complex planar pyrimidine moieties. This work provides the framework for new explorations into kinase inhibition and critical investigations into selectivity of inhibitory activity.

Tetrahedron published new progress about Heterocyclization. 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

Yang, Ruchun published the artcileDMSO/t-BuONa/O2-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles, Product Details of C8H8ClN, the main research area is quinoline preparation; tetrahydroquinoline sodium tert butoxide dimethyl sulfoxide oxidative dehydrogenation; isoquinoline preparation; tetrahydroisoquinoline sodium tert butoxide dimethyl sulfoxide oxidative dehydrogenation; indole preparation; indoline sodium tert butoxide dimethyl sulfoxide oxidative dehydrogenation.

Aromatic N-heterocycles such as quinolines I [R1 = H, 8-Cl, 6-OMe, etc.; R2 = H, 3-Me, 4-Ph, etc. X = N; Y = CH2], isoquinolines I [R1 = H; R2 = H, 1-Ph; X = CH2; Y = N] and indoles II [R1 = H, 5-F, 4-Br, etc.; R2 = H, 2-Me; Y = CH2, N] were synthesized via a sodium tert-butoxide promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution This reaction proceeded under mild reaction conditions with a good functional group tolerance. Mechanistic studies suggested a radical pathway involved hydrogen abstraction of dimsyl radicals from the N-H bond or α-C-H of the substrates, and subsequent oxidation of the nitrogen or α-aminoalkyl radicals.

Journal of Organic Chemistry published new progress about Indolines Role: RCT (Reactant), RACT (Reactant or Reagent). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Product Details of 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

Prusty, Namrata published the artcileSynthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations, Category: indole-building-block, the main research area is benzoindole preparation; indoline alkyne tandem reaction; polyarylcarbazole preparation regioselective; indole alkyne tandem reaction.

Nickel-catalyzed synthesis of polyarylcarbazoles I (R = H, Me; R1 = 4-F, 4-Cl, 4-Br, 5-Me, 5-OMe; R2 = C2H5, C6H5, 4-FC6H4, etc.) and II (R3 = 6-Br, 7-Cl, 8-Me, etc.) through sequential C-H bond activations has been described. Regioselective indole C2/C3 functionalization has been achieved in the presence of indoles III C7-H, which is quite challenging. In addition, this approach also gives easy access to building a heteropolycyclic motif through C6/C7 C-H functionalization of indolines IV. This methodol. is not limited to aromatic internal alkynes R2CCR2 as coupling partners; aliphatic alkynes have also shown good tolerance. Notably, during the optimization the catalytic enhancement with sodium iodide as an additive has been observed The photophys. properties of these highly conjugated mols. were obtained.

Organic Letters published new progress about C-H bond activation. 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

Ma, Rui-Jun published the artcileSynthesis of 1-benzylisoindoline and 1-benzyl-tetrahydroisoquinoline through nucleophilic addition of organozinc reagents to N,O-acetals, Category: indole-building-block, the main research area is benzylisoindoline preparation; benzyl tetrahydroisoquinoline preparation; organozinc compound acetal nucleophilic addition.

A new approach to access 1-benzylisoindolines I [n = 1, 2; R1 = Bn, 4-FC6H4CH2, 4-t-BuC6H4CH2, etc.; R2 = H, 5-Br, 6-Cl, etc.] and 1-benzyl-tetrahydroisoquinolines I [R2 = H, 6,7-di-OMe] was developed through nucleophilic addition of organozinc reagents to N,O-acetals. A number of substituted organozinc reagents were amenable for this transformation, and the desired products were obtained with excellent yields. Moreover, Sc(OTf)3 proved to be an effective catalyst for the formation of 1-benzylisoindolines I and 1-benzyl-tetrahydroisoquinolines II using such nucleophilic addition

Organic & Biomolecular Chemistry published new progress about Isoindoles Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 74572-29-5 belongs to class indole-building-block, name is 5-Chloroisoindolin-1-one, and the molecular formula is C8H6ClNO, 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