Month: October 2022

Ferreira, Everton Geraldo Capote; Gomes, Douglas Fabiano; Delai, Caroline Vanzzo; Barreiros, Marco Antonio Bacellar; Grange, Luciana; Rodrigues, Elisete Pains; Henning, Liliane Marcia Mertz; Barcellos, Fernando Gomes; Hungria, Mariangela published the artcile< Revealing potential functions of hypothetical proteins induced by genistein in the symbiosis island of Bradyrhizobium japonicum commercial strain SEMIA 5079 (= CPAC 15)>, Synthetic Route of 69205-79-4, the main research area is Bradyrhizobium genistein cobalamin amino acids symbiosis Squalene hopene cyclase; Biological nitrogen fixation; Functional inference; Gene expression; Symbiosis.

Bradyrhizobium japonicum strain SEMIA 5079 (= CPAC 15) is a nitrogen-fixing symbiont of soybean broadly used in com. inoculants in Brazil. Its genome has about 50% of hypothetical (HP) protein-coding genes, many in the symbiosis island, raising questions about their putative role on the biol. nitrogen fixation (BNF) process. This study aimed to infer functional roles to 15 HP genes localized in the symbiosis island of SEMIA 5079, and to analyze their expression in the presence of a nod-gene inducer. A workflow of bioinformatics tools/databases was established and allowed the functional annotation of the HP genes. Most were enzymes, including transferases in the biosynthetic pathways of cobalamin, amino acids and secondary metabolites that may help in saprophytic ability and stress tolerance, and hydrolases, that may be important for competitiveness, plant infection, and stress tolerance. Putative roles for other enzymes and transporters identified are discussed. Some HP proteins were specific to the genus Bradyrhizobium, others to specific host legumes, and the anal. of orthologues helped to predict roles in BNF. All 15 HP genes were induced by genistein and high induction was confirmed in five of them, suggesting major roles in the BNF process.

BMC Microbiology published new progress about Acacia auriculiformis. 69205-79-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C7H5N5O, Synthetic Route of 69205-79-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sakauchi, Nobuki; Kohara, Yasuhisa; Sato, Ayumu; Suzaki, Tomohiko; Imai, Yumi; Okabe, Yuichi; Imai, Shigemitsu; Saikawa, Reiko; Nagabukuro, Hiroshi; Kuno, Haruhiko; Fujita, Hisashi; Kamo, Izumi; Yoshida, Masato published the artcile< Discovery of 5-Chloro-1-(5-chloro-2-(methylsulfonyl)benzyl)-2-imino-1,2-dihydropyridine-3-carboxamide (TAK-259) as a Novel, Selective, and Orally Active α1D Adrenoceptor Antagonist with Antiurinary Frequency Effects: Reducing Human Ether-a-go-go-Related Gene (hERG) Liabilities>, Product Details of C8H6ClN, the main research area is adrenoceptor antagonist incontinence hERG; crystal structure adrenoceptor antagonist incontinence.

A novel structural class of iminopyridine derivative 1 was identified as a potent and selective human α1D adrenoceptor (α1D adrenergic receptor; α1D-AR) antagonist against α1A- and α1B-AR through screening of an inhouse compound library. From initial structure-activity relationship studies, we found lead compound 9m with hERG K+ channel liability. To develop analogs with reduced hERG K+ channel inhibition, a combination of site-directed mutagenesis and docking studies was employed. Further optimization led to the discovery of I and II, which showed antagonistic activity by a bladder strip test in rats with bladder outlet obstruction, as well as ameliorated cystitis-induced urinary frequency in rats. Ultimately, 9u was selected as a clin. candidate. This is the first study to show the utility of iminopyridine derivatives as selective α1D-AR antagonists and evaluate their effects in vivo.

Journal of Medicinal Chemistry published new progress about Androgen receptor antagonists. 21423-84-7 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H6ClN, Product Details of C8H6ClN.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sawyer, J. Scott; Schmittling, Elisabeth A.; Palkowitz, Jayne A.; Smith, William J. III published the artcile< Synthesis of diaryl ethers, diaryl thioethers, and diaryl amines mediated by potassium fluoride-alumina and 18-crown-6: Expansion of scope and utility>, Reference of 94087-40-8, the main research area is crown ether mediator aromatic substitution; potassium fluoride alumina mediator aromatic substitution; aniline aromatic substitution aryl halide; thiophenol aromatic substitution aryl halide; phenol aromatic substitution aryl halide; diaryl ether thioether preparation; arylamine preparation; ether diaryl preparation; thioether diaryl preparation; amine diaryl preparation; sulfide diaryl preparation.

An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diaryl amines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by KF-alumina/18-crown-6 in MeCN or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, electronically unfavorable 3-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.

Journal of Organic Chemistry published new progress about Aromatic amines Role: SPN (Synthetic Preparation), PREP (Preparation). 94087-40-8 belongs to class nitriles-buliding-blocks, and the molecular formula is C7H3ClFN, Reference of 94087-40-8.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Romagnoli, Romeo; Prencipe, Filippo; Oliva, Paola; Kimatrai Salvador, Maria; Brancale, Andrea; Ferla, Salvatore; Hamel, Ernest; Viola, Giampietro; Bortolozzi, Roberta; Persoons, Leentje; Balzarini, Jan; Liekens, Sandra; Schols, Dominique published the artcile< Design, synthesis and biological evaluation of 2-alkoxycarbonyl-3-anilinoindoles as a new class of potent inhibitors of tubulin polymerization>, Product Details of C8H8N2O, the main research area is alkoxycarbonyl anilinoindole preparation docking tubulin polymerization SAR antiproliferative human; Antiproliferative activity; Indole; Microtubules; Structure-activity relationship; Tubulin.

A new class of inhibitors of tubulin polymerization based on 2-alkoxycarbonyl-3-(3′,4′,5′-trimethoxyanilino)indole mol. skeleton I [R1 = H, 6-Cl, 5-MeO, etc.; R2 = Me, Et, iso-Pr, etc.; R3 = Me, Et, n-Pr, Bn; X = H, MeO] was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization and cell cycle effects. The results presented show that methoxy substitution and location on indole nucleus played an important role in inhibition of cell growth, and the most favorable position for substituent was at C-6. In addition, a small-size ester function (methoxy/ethoxycarbonyl) at 2-position of the indole core was desirable. Also, analogs that were alkylated with Me, Et or Pr groups or had a benzyl moiety on the N-1 indolic nitrogen retained activity equivalent to those observed in the parent N-1H analogs. The most promising compounds of series I [R1 = 5-MeO, R2 = Me, R3 = H, X = H; R1 = 6-MeO, R2 = R3 = Me, X = MeO] targeted tubulin at colchicine site with antitubulin activities comparable to that of reference compound combretastatin A-4.

Bioorganic Chemistry published new progress about Antiproliferative agents. 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Product Details of C8H8N2O.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Jia, Qianfa; Lan, Yunfei; Ye, Xin; Lin, Yinhe; Ren, Qiao published the artcile< Direct access to multi-functionalized benzenes via [4 + 2] annulation of α-cyano-β-methylenones and α,β-unsaturated aldehydes>, HPLC of Formula: 21667-62-9 , the main research area is cyano butanone propenal metal free regioselective cycloaddition reaction; benzene preparation.

An efficient [4 + 2] benzannulation of α-cyano-β-methylenones and α,β-unsaturated aldehydes was achieved under metal-free reaction conditions selectively delivering a wide range of polyfunctional benzenes in high yields resp. (up to 94% yield).

RSC Advances published new progress about [4+2] Cycloaddition reaction (regioselective). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, HPLC of Formula: 21667-62-9 .

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liu, Hui; Yan, Yingkun; Li, Min; Zhang, Xiaomei published the artcile< An enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived N-Boc ketimines>, Formula: C9H6ClNO, the main research area is isoxazole amino oxindole preparation enantioselective chiral phosphoric acid catalyst; aminoisoxazole isatin boc ketimine aza Friedel Crafts.

By employing a chiral phosphoric acid as a catalyst, an enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived N-Boc ketimines was realized. The reaction provided a wide variety of novel 3-isoxazole 3-amino-oxindoles I (R1 = C6H5, 4-OMeC6H4, 4-FC6H4, etc.; R2 = Me, Et, Bn, Allyl; R3 = H, 5-Me, 5-Cl, etc.; R4 = H, Me, Et, Bn, Boc) with good yields (up to 99%) and moderate to good enantioselectivities (up to 99%). The absolute configuration of one product was assigned by X-ray crystal structural anal. and a plausible reaction mechanism was proposed. In addition, a scale-up reaction was performed successfully. Finally, one product was subjected to Suzuki-Miyaura coupling with phenylboronic acid to afford the product in a moderate yield without erosion of the enantioselectivity.

Organic & Biomolecular Chemistry published new progress about Enantioselective synthesis. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Formula: C9H6ClNO.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Huang, Chun; Zhou, You; Yu, Xiao-Xiao; Wang, Li-Sheng; Wu, Yan-Dong; Wu, An-Xin published the artcile< I2/CuCl2-Copromoted Formal [4 + 1 + 1] Cyclization of Methyl Ketones, 2-Aminobenzonitriles and Ammonium Acetate: Direct Access to 2-Acyl-4-aminoquinazolines>, Electric Literature of 38487-85-3, the main research area is aminoquinazolinyl aryl methanone preparation; aryl ethanone aminobenzonitrile ammonium acetate cyclization.

An I2/CuCl2-copromoted diamination of C(sp3)-H bonds for the preparation of 2-acyl-4-aminoquinazolines I [Ar = Ph, 1-naphthyl, 4-MeOC6H4, etc.; R = 8-Me, 6-Cl, 7-MeO, etc.] from Me ketones, 2-aminobenzonitriles, and ammonium acetate was reported. This reaction featured operational simplicity, com. available substrates, mild reaction conditions, and good functional group compatibility. Mechanistic studies indicated that CuCl2 played a pivotal role in this transformation. This study uses a Me group as a novel input to construct 2-acyl-4-aminoquinazoline derivatives for the first time.

Journal of Organic Chemistry published new progress about Amination. 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Electric Literature of 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sen, Tejosmita; Neog, Kashmiri; Sarma, Sangita; Manna, Prasenjit; Deka Boruah, Hari Prasanna; Gogoi, Pranjal; Singh, Anil Kumar published the artcile< Efflux pump inhibition by 11H-pyrido[2,1-b]quinazolin-11-one analogues in mycobacteria>, Name: 3-Chloro-2-fluorobenzonitrile, the main research area is pyrido quinazolinone analog preparation efflux pump mycobacteria tuberculosis; Efflux pump; Efflux pump inhibitor; Fluoroquinolone resistance; Mycobacterium; Quinazolinone.

Mycobacterium tuberculosis infection causes 1.8 million deaths worldwide, of which half a million has been diagnosed with resistant tuberculosis (TB). Emergence of multi drug resistant and extensive drug resistant strains has made all the existing anti-TB therapy futile. The major involvement of efflux pump in drug resistance has made it a direct approach for therapeutic exploration against resistant M. tuberculosis. This study demarcates the role of 11H-pyrido[2,1-b]quinazolin-11-one (quinazolinone) analogs as efflux pump inhibitor in Mycobacterium smegmatis. Sixteen quinazolinone analogs were synthesized by treating 2-aminopyridine and 2-fluorobenzonitrile with KtOBu. Analogs were tested, and 3a, 3b, 3c, 3g, 3j, 3l, 3m, and 3p were found to modulate EtBr MIC by >4 whereas 3a, 3g, 3i and 3o showed >4 modulation on norfloxacin MIC. 3l and 3o in addition to their very low toxicity they showed high EtBr and norfloxacin accumulation resp. Time kill curve showed effective log reduction in colony forming unit in presence of these analogs, thus confirming their role as efflux pump inhibitor. Through docking and alignment studies, we have also shown that the LfrA amino acid residues that the analogs are interacting with are present in Rv2333c and Rv2846c of M. tuberculosis. This study have shown for the first time the possibility of developing the 11H-pyrido[2,1-b]quinazolin-11-one analogs as efflux pump inhibitors for M. smegmatis and hence unbolts the scope to advance this study against resistant M. tuberculosis as well.

Bioorganic & Medicinal Chemistry published new progress about Efflux pump inhibitors. 94087-40-8 belongs to class nitriles-buliding-blocks, and the molecular formula is C7H3ClFN, Name: 3-Chloro-2-fluorobenzonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Flemmich, Laurin; Moreno, Sarah; Micura, Ronald published the artcile< Synthesis of O6-alkylated preQ1 derivatives>, Computed Properties of 69205-79-4, the main research area is alkoxy pyrrolopyrimidinyl aminotrifluoroacetate salt preparation; RNA cofactors; RNA methylation; deazapurines; heterocycles; pyrrolopyrimidines; queuosine.

A robust synthesis for the class of pyrrolo[2,3-d]pyrimidines starting from readily accessible N2-pivaloyl-protected 6-chloro-7-cyano-7-deazaguanine. Substitution of the 6-chloro atom with the alcoholate of interest proceeded straightforward. The transformation of the 7-cyano substituent into the required aminomethyl group turned out to be challenging and was solved by a hydration reaction sequence on a well-soluble dimethoxytritylated precursor via in situ oxime formation. The synthetic path provided a solid foundation to access O6-alkylated 7-aminomethyl-7-deazaguanines for the development of RNA labeling tools based on the preQ1 class-I riboswitch scaffold.

Beilstein Journal of Organic Chemistry published new progress about Aliphatic amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 69205-79-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C7H5N5O, Computed Properties of 69205-79-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Browne, E. J. published the artcile< Perimidine-2-carbaldehyde>, Category: nitriles-buliding-blocks, the main research area is perimidinecarbaldehyde dimer; naphthalene diamino imidate condensation; imidate diaminonaphthalene condensation.

Perimidine-2-carbaldehyde was prepared and consists of a mixture of the free aldehyde (I, R = CHO) and the dimeric cyclic hemiaminal (II) in the solid state. This dimerization is analogous to that observed in many N-unsubstituted azole aldehydes. The aldehyde (I, R = CHO) initially forms as the hydrate (I, R = CH(OH)2) on hydrolysis of its diethyl acetal. The condensation of imidates or imidate salts with 1,8-diaminonaphthalene is a useful route to 2-substituted perimidines or their salts.

Australian Journal of Chemistry published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts