Tag: M.W=100-150

Inami, Kaoru; Shiba, Tetsuo published the artcile< Total synthesis of antibiotic althiomycin>, HPLC of Formula: 6136-93-2, the main research area is total synthesis althiomycin antibiotic.

Total synthesis of antibiotic althiomycin (I) was achieved staring from D-cysteine. The imide bond between thiazoline and the pyrrolinone part was constructed by coupling reaction of sodium salt of pyrrolinone with cysteine active ester or by photoreaction with diketene. The hydroxymethyl group attached on the carbon adjacent to C-2 of the thiazoline ring, was introduced by aldol condensation posterior to the thiazoline ring formation. The thiazole part was introduced in a final step in whole process of the total synthesis of the antibiotic. The synthetic althiomycin was identical with the natural antibiotic in all respects.

Bulletin of the Chemical Society of Japan published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, HPLC of Formula: 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Chen, Ying-Chu; Faver, John C.; Ku, Angela F.; Miklossy, Gabriella; Riehle, Kevin; Bohren, Kurt M.; Ucisik, Melek N.; Matzuk, Martin M.; Yu, Zhifeng; Simmons, Nicholas published the artcile< C-N Coupling of DNA-Conjugated (Hetero)aryl Bromides and Chlorides for DNA-Encoded Chemical Library Synthesis>, Category: nitriles-buliding-blocks, the main research area is DNA encoded heteroaryl amide library synthesis.

DNA-encoded chem. library (DECL) screens are a rapid and economical tool to identify chem. starting points for drug discovery. As a robust transformation for drug discovery, palladium-catalyzed C-N coupling is a valuable synthetic method for the construction of DECL chem. matter; however, currently disclosed methods have only been demonstrated on DNA-attached (hetero)aromatic iodide and bromide electrophiles. We developed conditions utilizing an N-heterocyclic carbene-palladium catalyst that extends this reaction to the coupling of DNA-conjugated (hetero)aromatic chlorides with (hetero)aromatic and select aliphatic amine nucleophiles. In addition, we evaluated steric and electronic effects within this catalyst series, carried out a large substrate scope study on two representative (hetero)aryl bromides, and applied this newly developed method within the construction of a 63 million-membered DECL.

Bioconjugate Chemistry published new progress about Anilines Role: CMB (Combinatorial Study), RCT (Reactant), RACT (Reactant or Reagent). 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Li, Quanzhe; Liu, Jiaxin; Wei, Yin; Shi, Min published the artcile< One-Pot Synthesis of Spirocyclopenta[a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization>, Application In Synthesis of 38487-85-3, the main research area is spirocyclopentaindene derivative preparation; propargyl alc tethered alkylidenecyclobutane preparation cascade ring expansion cyclization.

A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramol. Friedel-Crafts-type cyclization from propargyl alc.-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments

Journal of Organic Chemistry published new progress about Alcohols, propargyl Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Application In Synthesis of 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Utimoto, Kiitiro; Wakabayashi, Yukio; Shishiyama, Yuho; Inoue, Masaharu; Nozaki, Hitosi published the artcile< 2-Alkoxy- and 2,2-dialkoxynitriles from acetals and ortho esters: exchange of alkoxy into cyano group by means of cyanotrimethylsilane>, Name: 2,2-Diethoxyacetonitrile, the main research area is acetal aromatic aliphatic cyanation; ortho ester cyanation catalyst; tin fluoroborane cyanation catalyst; borane fluoro catalyst cyanation; alkoxynitrile; nitrile alkoxy; methoxyacetonitrile lithiation octylation oxidation; acetonitrile methoxy lithiation octylation oxidation; nonanoate.

Thirteen RCR1(OR2)CN (R = H, alkyl, Ph, PhCH2; R1 = H, OMe, OEt; R2 = Me, Et) were prepared in 64-97% yield by cyanation of the corresponding RCR1(OR2)2 with Me3SiCN in the presence of SnCl2 or BF3.OEt2 catalysts. E.g., 80% (MeO)2CHCN (I) was obtained on treatment of (MeO)3CH with 1 equiv Me3SiCN and a catalytic amount of BF3.OEt2 at room temperature I was converted to Me(CH2)7CO2Me by sequential treatment with LiN(CHMe2)2, Me(CH2)7Br, and p-MeC6H4SO3H in Me2CO-H2O.

Tetrahedron Letters published new progress about Acetals Role: RCT (Reactant), RACT (Reactant or Reagent). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Name: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hattori, Yohei; Nishikawa, Michihiro; Kusamoto, Tetsuro; Kume, Shoko; Nishihara, Hiroshi published the artcile< Steric interference on the redox-conjugated pyrimidine ring rotation of mono- and dinuclear copper complexes with (4-methyl-2-pyrimidinyl)imine ligands>, Application of C6H11NO2, the main research area is copper phenanthroline methylpyrimidinylmethylene benzeneamine complex preparation; electrochem copper phenanthroline methylpyrimidinylmethylene benzeneamine complex; crystal structure copper phenanthroline methylpyrimidinylmethylene benzeneamine complex.

A mononuclear copper(I) complex with N-[(4-methyl-2-pyrimidinyl)methylene]-p-toluidine (1·BF4; [(Phen-anth2)Cu(L1)]·BF4) and a dinuclear copper(I) complex with N,N’-bis[(4-methyl-2-pyrimidinyl)-methylene]-p-phenylenediamine (2·(BF4)2; [(Phen-anth2)2Cu2(μ-L2)]·(BF4)2) (where Phen-anth2 = dianthracenylphenathroline, L1 = N-[(4-methyl-2-pyrimidinyl)methylene]-p-toluide and L2 = N,N’-bis[(4-methyl-2-pyrimidinyl)methylene]-p-phenylenediamine) were synthesized as BF4- salts to evaluate the influence of the imine moiety on the pyrimidine ring rotation isomerism. 1·BF4 existed in solution as a mixture of two isomers; 2·(BF4)2 was present as a mixture of three isomers. The redox potentials of the copper centers were changed by pyrimidine ring rotation. Comparison of 1+ and 22+ indicated that increasing the steric congestion around the copper center increased the o/i isomer ratio; the redox potentials of both the o- and i-isomers shifted in the pos. direction, and the CuII/I redox reaction became slower.

Chemistry Letters published new progress about Conformational transition, ring inversion (kinetics). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Application of C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Green, Neal; Hu, Yonghan; Janz, Kristin; Li, Huan-Qiu; Kaila, Neelu; Guler, Satenig; Thomason, Jennifer; Joseph-McCarthy, Diane; Tam, Steve Y.; Hotchandani, Rajeev; Wu, Junjun; Huang, Adrian; Wang, Qin; Leung, Louis; Pelker, Jefferey; Marusic, Suzana; Hsu, Sang; Telliez, Jean-Baptiste; Hall, J. Perry; Cuozzo, John W.; Lin, Lih-Ling published the artcile< Inhibitors of Tumor Progression Loci-2 (Tpl2) Kinase and Tumor Necrosis Factor α (TNF-α) Production: Selectivity and in Vivo Antiinflammatory Activity of Novel 8-Substituted-4-anilino-6-aminoquinoline-3-carbonitriles>, COA of Formula: C6H11NO2, the main research area is anilinoaminoquinoline carbonitrile derivative preparation structure Tpl2 kinase inhibitor antiinflammatory.

Tumor progression loci-2 (Tpl2) (Cot/MAP3K8) is a serine/threonine kinase in the MAP3K family directly upstream of MEK. Recent studies using Tpl2 knockout mice have indicated an important role for Tpl2 in the lipopolysaccharide (LPS) induced production of tumor necrosis factor α (TNF-α) and other proinflammatory cytokines involved in diseases such as rheumatoid arthritis. Initial 4-anilino-6-aminoquinoline-3-carbonitrile leads showed poor selectivity for Tpl2 over epidermal growth factor receptor (EGFR) kinase. Using mol. modeling and crystallog. data of the EGFR kinase domain with and without an EGFR kinase-specific 4-anilinoquinazoline inhibitor (erlotinib, Tarceva), the authors hypothesized that the authors could diminish the inhibition of EGFR kinase by substitution at the C-8 position of the 4-anilino-6-aminoquinoline-3-carbonitrile leads. The 8-substituted-4-anilino-6-aminoquinoline-3-carbonitriles were prepared from the appropriate 2-substituted 4-nitroanilines. Modifications to the C-6 and C-8 positions led to the identification of compounds with increased inhibition of TNF-α release from LPS-stimulated rat and human blood, and these analogs were also highly selective for Tpl2 kinase over EGFR kinase. Further structure-activity based modifications led to the identification of 8-bromo-4-(3-chloro-4-fluorophenylamino)-6-[(1-methyl-1H-imidazol-4-yl)methylamino]quinoline-3-carbonitrile, which demonstrated in vitro as well as in vivo efficacy in inhibition of LPS-induced TNF-α production

Journal of Medicinal Chemistry published new progress about Anti-inflammatory agents. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, COA of Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Gao, Xiang; Liu, Jiao; Liu, Zhaopeng; Zhang, Lei; Zuo, Xin; Chen, Leyuan; Bai, Xue; Bai, Qingyun; Wang, Xinlin; Zhou, Anning published the artcile< DBU coupled ionic liquid-catalyzed efficient synthesis of quinazolinones from CO2 and 2-aminobenzonitriles under mild conditions>, Recommanded Product: 2-Amino-4-methoxybenzonitrile, the main research area is quinazolinone preparation organic base ionic liquid catalyst; aminobenzonitrile carbon dioxide cyclization diazabicycloundecene ionic liquid catalyst.

An efficient catalytic system of organic base-coupled ionic liquids (ILs) that could catalyze the synthesis of quinazolinones I (R1 = H, OMe, Cl, Br, R2 = H; R1 = H, R2 = Cl) via cyclization of 2-aminobenzonitriles with CO2 under mild conditions (e.g., 60°C, 0.1 MPa) was reported. It was found that 1,8-diazabicyclo[5.4.0]undec-7-ene coupled with 1-butyl-3-methylimidazole acetate ionic liquids, (DBU/[Bmim][OAc]), displayed excellent performance in catalyzing the reactions of CO2 with 2-aminobenzonitriles to give compounds I in high yields at atm. pressure. Moreover, the ILs had high stability and reusability, and could be reused at least five times without considerable decrease in catalytic activity. This protocol could also be conducted on a gram scale, and may have promising and practical applications in the production of quinazolinones.

RSC Advances published new progress about Aromatic nitriles Role: RCT (Reactant), RACT (Reactant or Reagent) (amino). 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Recommanded Product: 2-Amino-4-methoxybenzonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ruske, Walter; Becker, Manfred; Jahns, Hans Joachim published the artcile< Polymerization mechanisms of hydrocyanic acid. II. Reaction of negatively disubstituted acetonitriles with ammonia>, Application In Synthesis of 6136-93-2, the main research area is .

Cl2CHCN and NH3 form 2,4,6-tris(dichloromethyl)-1,3,5-triazine and a black-brown polymer (I). Its infrared spectrum coincides with that of the polymer formed from dichloroacetamidine and NH3 and is very similar to the spectrum of paracyanogen. Elementary analysis of I shows the presence of O, probably introduced by hydrolysis. Polymerization of diethoxyacetonitrile, which has a lesser inductive effect of its C-X dipole than the dichloro compound, does not lead to tris(diethoxymethyl)-1,3,5-triazine. These 2 cases permit a general prediction about the course of the polymerization mechanism of HCN. The reaction has the same selectivity towards the catalyst as the benzoin condensation; the real catalyst is the cyanide ion.

Zeitschrift fuer Chemie published new progress about IR spectra. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Application In Synthesis of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Anthony, Nahoum G.; Breen, David; Clarke, Joanna; Donoghue, Gavin; Drummond, Allan J.; Ellis, Elizabeth M.; Gemmell, Curtis G.; Helesbeux, Jean-Jacques; Hunter, Iain S.; Khalaf, Abedawn I.; Mackay, Simon P.; Parkinson, John A.; Suckling, Colin J.; Waigh, Roger D. published the artcile< Antimicrobial Lexitropsins Containing Amide, Amidine, and Alkene Linking Groups>, Category: nitriles-buliding-blocks, the main research area is lexitropsin antibiotic antimicrobial antibacterial agent preparation; distamycin analog lexitropsin antimicrobial antibacterial agent preparation; thiazotropsin analog lexitropsin antimicrobial antibacterial agent prepare; fungicide lexitropsin antimicrobial distamycin analog preparation.

The synthesis and properties of 80 short minor groove binders, such as I, related to distamycin and the thiazotropsins were described. The design of the compounds was principally predicated upon increased affinity arising from hydrophobic interactions between minor groove binders and DNA. The introduction of hydrophobic aromatic head groups, including quinolyl and benzoyl derivatives, and of alkenes as linkers led to several strongly active antibacterial compounds with MIC for Staphylococcus aureus, both methicillin-sensitive and -resistant strains, in the range of 0.1-5 μg mL-1, which is comparable to many established antibacterial agents. Antifungal activity was also found in the range of 20-50 μg mL-1 MIC against Aspergillus niger and Candida albicans, again comparable with established antifungal drugs. A quinoline derivative was found to protect mice against S. Aureus infection for a period of up to six days after a single i.p. dose of 40 mg kg-1.

Journal of Medicinal Chemistry published new progress about Antibacterial agents. 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

Deng, Guobo; Zhong, Ronglin; Song, Jianxin; Choy, Pui Ying; Kwong, Fuk Yee published the artcile< Assembly of Furazan-Fused Quinolines via an Expeditious Metal-Free [2+2+1] Radical Tandem Cyclization Process>, Related Products of 38487-85-3, the main research area is oxadiazoloquinoline preparation; arylketimine benzonitrile tertbutyl nitrite radical tandem heteroannulation.

A [2+2+1]-NO-segment-incorporating heteroannulative cascade is described. This versatile method, particularly using modular cyanoarylated ketimine substrates 2-CN-3-R-4-R1-5-R2C6HN=C(Me)Ar (Ar = 3-methylphenyl, 4-bromophenyl, thiophen-2-yl, etc.; R = H, Br; R1 = H, Br; R2 = H, Me, F, Cl, Br, MeO, CF3), allows efficient access to structurally diversified quinolines embedded with an oxadiazole core I. This metal-free protocol proceeds smoothly at 30°C, offers easy manipulation of substituents on the quinoline moiety, and tolerates a spectrum of functional groups. D. functional theory calculation revealed that the cyano moiety is crucial to facilitate the early cyclization step in this heteroannulation process and is different from the previously established late cyclization mechanistic interpretation.

Organic Letters published new progress about Density functional theory, B3LYP. 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Related Products of 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts