Tag: M.W:100-200

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 17190-29-3, is researched, Molecular C9H9NO, about Unexpected Stereorecognition in Nitrilase-Catalyzed Hydrolysis of β-Hydroxy Nitriles, the main research direction is nitrile hydroxy preparation enantioselective enzymic hydrolysis nitrilase; carboxylic acid hydroxy aryl asym synthesis.Recommanded Product: 17190-29-3.

Biocatalytic enantioselective hydrolysis of β-hydroxy nitriles RCH(OH)CH2CN (R = Ph, 4-FC6H4, 2-MeOC6H4, 2,4-Cl2C6H3, etc.) to the corresponding (S)-enriched β-hydroxy carboxylic acids RCH(OH)CH2COOH has been achieved for the first time by an isolated nitrilase bll6402 from Bradyrhizobium japonicum USDA110. This offers a new “”green”” approach to optically pure β-hydroxy nitriles and β-hydroxy carboxylic acids. The observed remote stereorecognition is surprising because this nitrilase shows no enantioselectivity for the hydrolysis of α-hydroxy nitriles such as mandelonitrile.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Applied Microbiology and Biotechnology called Characterisation of nitrilase and nitrile hydratase biocatalytic systems, Author is Brady, D.; Beeton, A.; Zeevaart, J.; Kgaje, C.; van Rantwijk, F.; Sheldon, R. A., which mentions a compound: 17190-29-3, SMILESS is N#CCC(O)C1=CC=CC=C1, Molecular C9H9NO, Name: 3-Hydroxy-3-phenylpropanenitrile.

Biocatalytic transformations converting aromatic and arylaliph. nitriles into the analogous related amide or acid were investigated. These studies included synthesis of the β-substituted nitrile 3-hydroxy-3-phenylpropionitrile, subsequent enrichment and isolation on this substrate of nitrile-degrading microorganisms from the environment, and a comparative study of enzymic reactions of nitriles by resting cell cultures and enzymes. Each biocatalyst exhibited a distinctive substrate selectivity profile, generally related to the length of the aliphatic chain of the arylaliph. nitrile and the position of substituents on the aromatic ring or aliphatic chain. Cell-free nitrilases generally exhibited a narrower substrate range than resting whole cells of Rhodococcus strains. The Rhodococcus strains all exhibited nitrile hydratase activity and converted β-hydroxy nitriles (but did not demonstrate enantioselectivity on this substrate). The biocatalysts also mediated the synthesis of a range of α-hydroxy carboxylic acids or amides from aldehydes in the presence of cyanide. The use of an amidase inhibitor permits halting the nitrile hydratase/amidase reaction at the amide intermediate.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Fluoro-1H-indole-3-carboxylic acid, is researched, Molecular C9H6FNO2, CAS is 23077-42-1, about Amphiphilic Indole Derivatives as Antimycobacterial Agents: Structure-Activity Relationships and Membrane Targeting Properties, the main research direction is antimycobacterial membrane targeting indole preparation structure activity.Formula: C9H6FNO2.

Antibacterials that disrupt cell membrane function have the potential to eradicate “”persister”” organisms and delay the emergence of resistance. Here we report the antimycobacterial activities of 4-fluoro and 6-methoxyindoles bearing a cationic amphiphilic motif represented by a lipophilic n-octyl side chain at position 1 and a pos. charged azepanyl or 1,4-dioxa-8-azaspiro[4.5]decane moiety at position 3. These analogs exhibited balanced profiles of potency (Mycobacterium bovis BCG, M tuberculosis H37Rv), selective activity, solubility, and metabolic stability. Bacteriol. mechanism of action investigations on a representative analog revealed cell membrane permeabilization and depolarization in M bovis BCG. These membrane-related changes preceded cell death indicating that the loss in membrane integrity was not an epiphenomenon. Bactericidal activity was observed against both growing and nongrowing mycobacterial cultures. The analog also upregulated cell envelope stress-inducible promoters piniBAC and pclgR, implicating the involvement of envelope-related targets in its mode of action.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 17190-29-3, is researched, Molecular C9H9NO, about Direct Catalytic Aldol-Type Reactions Using RCH2CN, the main research direction is beta hydroxynitrile preparation; copper catalyst trimethylsilylacetonitrile alkyl nitrile aldehyde ketone; phosphine ligand copper catalyzed addition alkyl nitrile aldehyde ketone; triethoxysilyl fluoride reagent copper catalyzed addition trimethylsilylacetonitrile aldehyde ketone; enantioselective addition acetonitrile trimethylsilylacetonitrile aldehyde copper catalyst nonracemic binaphthylphosphine; direct catalytic aldol addition reaction nitrile.Synthetic Route of C9H9NO.

β-Hydroxynitriles are prepared from either trimethylsilylacetonitrile or from alkyl nitriles in the presence of copper catalysts; in the presence of nonracemic ligands, the copper-catalyzed addition of acetonitrile or trimethylsilylacetonitrile yields nonracemic β-hydroxynitriles in moderate enantioselectivities and yields. α-Unsubstituted-β-hydroxynitriles are prepared in 75-100% yields by the addition of trimethylsilylacetonitrile to aldehydes and ketones in the presence of copper fluoride and a stoichiometric quantity of triethoxysilyl fluoride; the reaction is effective for aryl ketones and aldehydes, alkyl and cycloalkyl aldehydes, and α,β-unsaturated aldehydes and ketones. α-Unsubstituted- and α-substituted-β-hydroxynitriles are prepared in 71-95% yields by the addition of alkyl nitriles RCH2CN (R = H, Me, Et) to aldehydes in the presence of alk. metal-free copper (I) tert-butoxide (generated by addition of tert-butanol to mesitylcopper) and a phosphine such as dppe; α-substituted-β-hydroxynitriles are generated with moderate to low stereoselectivities for the syn isomers. Hydrolysis of the nitriles to carboxylic acids with base allows the addition of nitriles to aldehydes and ketones to function as a catalytic surrogate for the aldol addition reaction of esters to ketones and aldehydes. In the presence of nonracemic diphosphine ligands and either copper (I) tert-butoxide or copper (I) fluoride and triethoxysilyl fluoride, either acetonitrile or trimethylsilylacetonitrile, resp., add enantioselectively to aldehydes or ketones to give β-hydroxynitriles in 48-70% yields and in 47-53% ee.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 17190-29-3. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Synthetic application of cyanoaminosilanes as azomethine ylide equivalents. Author is Padwa, Albert; Chen, Yon Yih; Dent, William; Nimmesgern, Hildegard.

A series of α-cyanoaminosilanes acted as azomethine ylide equivalent Treatment of these compounds with AgF in the presence of electron-deficient alkynes and olefins gives substituted pyrroles and pyrrolidines in high yield. Me3SiCH2N(CH2Ph)CH2CN (I) undergoes stereospecific cycloaddition with di-Me fumarate and maleate. The stereospecificity of the reaction is consistent with a concerted cycloaddition reaction. The cycloaddition behavior of an unsym. substituted α-cyanosilylamine with MeO2CCCH was also examined and found to react with high overall regioselectivity. The synthetic utility of cyanoaminosilanes as azomethine ylide equivalent was demonstrated by the preparation of a Reniera isoindole alkaloid (II). The key step in the synthesis involved the reaction of 2-methyl-3-methoxyquinone with I in the presence of AgF to give 2,5-dimethyl-6-methoxyisoindole-4,7-dione in good yield.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Recommanded Product: 22600-77-7. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (1H-Imidazol-2-yl)methanamine dihydrochloride, is researched, Molecular C4H9Cl2N3, CAS is 22600-77-7, about Development of Selective Clk1 and -4 Inhibitors for Cellular Depletion of Cancer-Relevant Proteins. Author is ElHady, Ahmed K.; Abdel-Halim, Mohammad; Abadi, Ashraf H.; Engel, Matthias.

In cancer cells, kinases of the Clk family control the supply of full-length, functional mRNAs coding for a variety of proteins essential to cell growth and survival. Thus, inhibition of Clks might become a novel anticancer strategy, leading to a selective depletion of cancer-relevant proteins after turnover. On the basis of a Weinreb amide hit compound, the authors designed and synthesized a diverse set of methoxybenzothiophene-2-carboxamides, of which the N-benzylated derivative showed enhanced Clk1 inhibitory activity. Introduction of a m-fluorine in the benzyl moiety eventually led to the discovery of compound 21b (5-methoxybenzo[b]thiophene-2-carboxylic acid (3-fluorobenzyl)methylamide), a potent inhibitor of Clk1 and -4 (IC50 = 7 and 2.3 nM, resp.), exhibiting an unprecedented selectivity over Dyrk1A. Compound 21b triggered the depletion of EGFR, HDAC1, and p70S6 kinase from the cancer cells, with potencies in line with the measured GIC50 values. In contrast, the cellular effects of congener 21a (5-methoxybenzo[b]thiophene-2-carboxylic acid 3-fluorobenzylamide), which inhibited Clk1 only weakly, were substantially lower.

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Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Category: pyrazoles-derivatives. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Reformatskii type additions of haloacetonitriles to aldehydes mediated by metallic nickel. Author is Inaba, Shinichi; Rieke, Reuben D..

β-Hydroxy nitriles HOCHRCH2CN [R = (un)substituted Ph, styryl, alkyl, alkenyl] were prepared by Reformatskii type addition of haloacetonitriles to aldehydes RCHO in the presence of metallic Ni (generated in situ).

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Preparation of β-hydroxyesters from isoxazolines. A selective Ni0bpy-catalyzed electrochemical method, published in 2003-11-03, which mentions a compound: 17190-29-3, Name is 3-Hydroxy-3-phenylpropanenitrile, Molecular C9H9NO, Quality Control of 3-Hydroxy-3-phenylpropanenitrile.

An electrocatalytic method for the reductive N-O cleavage of isoxazolines I [R1 = Ph; R2 = H; R3 = OMe, Br; R1R2 = (CH2)4; R3 = OMe], is described. Ni0bpy, generated in situ, was used to promote selective ring opening of I. DMF and NaI were used as solvent and supporting electrolyte resp., and β-hydroxyesters were obtained in high yields, after acid hydrolysis. β-Hydroxynitriles were also identified as side products.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Category: pyrazoles-derivatives. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Addition of α-Halo-substituted Carbonitriles to Aldehydes and Ketones in the Presence of Iron Pentacarbonyl.

Halo-substituted carbonitriles in the presence of iron pentacarbonyl react with aldehydes and ketones by Reformatsky reaction type. In contract to halo-substituted esters the nitriles are considerably more reactive toward ketones than aldehydes. At the same time the structure and yield of products obtained from both nitriles and esters are strongly and similarly affected by the character of the para-substituents in the benzaldehyde. Thus, Fe(CO)5-mediated reaction of ICH2CN with 2-hexanone in C6H6 gave 70% 3-hydroxy-3-methylenanthonitrile.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Quality Control of 4-Fluoro-1H-indole-3-carboxylic acid. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-Fluoro-1H-indole-3-carboxylic acid, is researched, Molecular C9H6FNO2, CAS is 23077-42-1, about Synthesis and Pharmacological Evaluation of Heterocyclic Carboxamides: Positive Allosteric Modulators of the M1 Muscarinic Acetylcholine Receptor with Weak Agonist Activity and Diverse Modulatory Profiles. Author is Dallagnol, Juliana C. C.; Khajehali, Elham; van der Westhuizen, Emma T.; Jorg, Manuela; Valant, Celine; Goncalves, Alan G.; Capuano, Ben; Christopoulos, Arthur; Scammells, Peter J..

Targeting allosteric sites at M1 muscarinic acetylcholine receptors is a promising strategy for the treatment of Alzheimer’s disease. Pos. allosteric modulators not only may potentiate binding and/or signaling of the endogenous agonist acetylcholine (ACh) but also may possess direct agonist activity (thus referred to as PAM-agonists). Recent studies suggest that PAM-agonists with robust intrinsic efficacy are more likely to produce adverse effects in vivo. Herein we present the synthesis and pharmacol. evaluation of a series of pyrrole-3-carboxamides with a diverse range of allosteric profiles. We proposed structural modifications at top, core, or pendant moieties of a prototypical mol. Although generally there was a correlation between the degree of agonist activity and the modulatory potency of the PAMs, some derivatives displayed weak intrinsic efficacy yet maintained strong allosteric modulation. We also identified mols. with the ability to potentiate mainly the affinity or both affinity and efficacy of ACh.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics