Category: nitriles-buliding-blocks

Zou, Shuping published the artcileA integrated process for nitrilase-catalyzed asymmetric hydrolysis and easy biocatalyst recycling by introducing biocompatible biphasic system, COA of Formula: C8H6ClNO, the publication is Bioresource Technology (2021), 320(Part_B), 124392, database is CAplus and MEDLINE.

The whole-cell nitrilase-catalyzed asym. hydrolysis of nitriles is a green and efficient preparation approach for chiral carboxylic acids, but often suffers from toxicity and cell lysis from organic substrates. In this work, a novel integrated process for whole-cell nitrilase-catalyzed asym. hydrolysis was developed for the first time by introducing a biocompatible ionic liquid (IL)-based biphasic system. The whole-cell nitrilases displayed an outstanding stability and recyclability in the biphasic system and still retained > 85% activity even after 7 cycles reaction. A preparative-scale fed-batch hydrolysis of o-chloromandelonitrile to (R)-o-chloromandelic acid (R-CMA) was performed using the integrated process. The results revealed a yield of 91.3% and a space-time yield of 746.4 g·L^-1·d^-1, which are currently the highest reported values for R-CMA biosynthesis. The proposed integrated process avoids substrate inhibition, facilitates the reusability of whole-cell nitrilases, and thus shows great potential for the sustainable production of chiral carboxylic acids.

Bioresource Technology published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C6H5F4NO3S, COA of Formula: C8H6ClNO.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Liu, Tao published the artcileDesign, Synthesis, and Biological Evaluation of Novel 4-Aminopiperidinyl-linked 3,5-Disubstituted-1,2,6-thiadiazine-1,1-dione Derivatives as HIV-1 NNRTIs, Safety of 2-(Chloromethyl)benzonitrile, the publication is Chemical Biology & Drug Design (2015), 86(1), 887-893, database is CAplus and MEDLINE.

A novel series of 4-aminopiperidinyl-linked 3,5-disubstituted-1,2,6-thiadiazine-1,1-dione derivatives I [R = 3-CN, 4-NO₂, 2,4,6-(CH₃)₃, etc.; Ar = 1-naphthyl, 2,4-dichlorophenyl] were designed, synthesized, and evaluated for their in vitro anti-HIV activities in MT-4 cells based on the hybridization of the privileged fragments in DABO and DAPY-typed HIV-1 NNRTIs. Most of the target compounds showed weak inhibitory activity against WT HIV-1. In order to confirm the mode of action of the target compounds, representative compounds I (R = 4-NO₂; Ar = 1-naphthyl) and I (R = 4-NO₂; Ar = 2,4-dichlorophenyl) were selected to perform the HIV-1 RT inhibitory assay. In this assay, I (R = 4-NO₂; Ar = 1-naphthyl) and I (R = 4-NO₂; Ar = 2,4-dichlorophenyl) displayed good activity with IC₅₀ values of 3.15 and 1.52 μM, resp. Addnl., preliminary structure-activity relationships (SARs) anal. and mol. docking studies of newly synthesized compounds were also discussed.

Chemical Biology & Drug Design published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Safety of 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wang, Jian-Shu published the artcileEx Situ Generation of Difluorodiazoethane (CF₂HCHN₂): Application in the Regioselective Synthesis of CF₂H-Containing Pyrazoles, HPLC of Formula: 5153-73-1, the publication is Organic Letters (2019), 21(21), 8751-8755, database is CAplus and MEDLINE.

A new method for the ex situ generation of difluorodiazoethane (CF₂HCHN₂) and a procedure for its efficient use in [3 + 2] cycloaddition with nitroolefins by the AcOH/O₂ catalyst system were developed by using a simple two-chamber system. The method provides a facile and straightforward access to a series of 4-substituted 5-difluoromethyl-3-nitro-1H-pyrazoles that are of interest in medicinal chem. Interestingly, the key factor for the success of this method is the efficient preparation of CF₂HCHN₂ by an ex situ process.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C8H7N3, HPLC of Formula: 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Zheng, Changge published the artcileGeometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF₃ for (E)-Vinyl Trifluoromethyl Thioethers, Application In Synthesis of 5153-73-1, the publication is Organic Letters (2020), 22(12), 4868-4872, database is CAplus and MEDLINE.

An efficient copper(II)-promoted denitrative trifluoromethylthiolation under mild reaction conditions has been developed for vinyl trifluoromethyl thioethers to construct C_vinyl-SCF₃ bonds with stable AgSCF₃ as a source of the trifluoromethylthio. This reaction system tolerates a broad range of functional groups to commendably achieve a high product yield and excellent stereoselectivity of E/Z.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C24H29N5O3, Application In Synthesis of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Han, Xinya published the artcileBiological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase, Formula: C9H6N2O2, the publication is Bioorganic & Medicinal Chemistry (2020), 28(18), 115624, database is CAplus and MEDLINE.

Herein, a series of nitrostyrene derivatives I (R¹ = H, F, Me, etc.; R² = H, Cl, Me, etc.; R³ = H, Cl, Br, Me) were synthesized, and their inhibitory activities against Fructose-1,6-bisphosphatase (FBPase) were investigated in vitro. Most of the prepared compounds exhibit potent FBPase inhibition (IC₅₀ < 10μM). Specifically, when the substituents of F, Cl, OMe, CF₃, OH, CO₂H, or 2-nitrovinyl were installed at the R² (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5-55 folds compared to those compounds with the same groups at the R¹ (para-) position. In addition, the preferred substituents at the R³ position were Cl or Br, thus compound I (R¹ = NO₂; R² = H; R³ = Cl) exhibited the most potent inhibitory activity (IC₅₀ = 0.15μM). The mol. docking and site-directed mutation suggest that C128 and N125 are essential for the binding of I (R¹ = NO₂; R² = H; R³ = Cl) and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R³ position is Cl > H > CH₃. CoMSIA anal. is consistent with proposed binding mode. The effect of compounds I (R¹ = 1,2,4-triazol-1-yl; R² = H; R³ = H) and I (R¹ = NO₂; R² = H; R³ = Cl) on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100μM, resp.

Bioorganic & Medicinal Chemistry published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Formula: C9H6N2O2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Moreland, D. E. published the artcileComparative effects of dichlobenil and its phenolic alteration products on photo- and oxidative phosphorylation, Name: 2,6-Dichloro-3-hydroxybenzonitrile, the publication is Pesticide Biochemistry and Physiology (1974), 4(3), 356-64, database is CAplus.

The effects of dichlobenil (2,6-dichlorobenzonitrile)(I) [1194-65-6] and its phenolic degradation products, 2,6-dichloro-3-hydroxybenzonitrile (II) [3336-34-3] and 2,6-dichloro-4-hydroxybenzonitrile (III) [3336-19-4] on electron transport and phosphorylation were studied in isolated spinach (Spinacia oleracea) chloroplasts and mung bean (Phaseolus aureus) mitochondria. II and III inhibited photoreduction, coupled phosphorylation, and cyclic phosphorylation in chloroplasts and acted as uncouplers of oxidative phosphorylation in mitochondria. II and III also decreased ATP in mung bean hypocotyls. In all assays only limited inhibition was caused by I, even at relatively high concentrations (1.0 mM).

Pesticide Biochemistry and Physiology published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, Name: 2,6-Dichloro-3-hydroxybenzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Barnathan, Gilles published the artcileSynthesis of C-nucleosides. XI. 2-D-Arabinofuranosylimidazoles and 8-D-arabinofuranosylpurines, Related Products of nitriles-buliding-blocks, the publication is European Journal of Medicinal Chemistry (1976), 11(1), 67-72, database is CAplus.

The nucleoside analogs I (R = NH2, SH, R1 = H) were prepared by treating II (R1 = R2 = Bz, R3 = Cl, Br) with Hg(CN)2, cleaving benzoyl groups from II (R1 = R2 = Bz, R3 = CN), treating II (R1 = Bz, R2 = H, R3 = CN) with PhCH2SH, cyclizing II (R1 = Bz, R2 = H, R3 = CH(:NH)SCH2Ph) with H2NCH(CN)2, cyclizing II (R1 = Bz, R2 =H, R3 = 4-cyano-5-amino-2-imidazolyl) with HC(:NH)NH2 or HC(OEt)3 and NaSH, and cleaving the benzoyl groups from I (R1 = Bz).

European Journal of Medicinal Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kumar, Arvind published the artcileKetene dithioacetals. Part 11. Reaction of 3-cyano-4-methylthio-2(1H)-pyridones with hydrazine and guanidine: synthesis of novel substituted and fused pyrazolo[4,3-c]pyridone and pyrido[4,3-d]pyrimidine derivatives, HPLC of Formula: 57663-05-5, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1978), 857-62, database is CAplus.

The N-methylpyridones I [R = Me, R¹ = H, R² = 4-R³C₆H₄, R³ = H, Me, MeO, Cl, Br; R = R² = Me, R¹ = H; R = Me, R¹R² = (CH₂)₃, (CH₂)₄] and the benzoquinolone II (R = Me, R¹ = H, n = 1) were prepared by alkylation of I (R = H, R¹, R² as before) and II (R = R¹ = H, n = 1), resp., with Me₂SO₄-NaOMe, followed by heating the mixture of N-Me and O-Me products with MeI. Treatment of I (R = H, Me, R¹ = H, R² = 4-R³C₆H₄, R³ = H, Me, MeO, Cl, Br; R = R² = Me, R¹ = H; R = R¹ = H, R² = 3-, 4-pyridyl; R = H, R¹ = Ph, R² = Me) with NH₂NH₂ in refluxing Me₂CHOH gave 70-90% pyrazolopyridones III. Similar treatment of I [R = H, Me, R¹R² = (CH₂)₃, (CH₂)₄; R = H, R¹R² = (CH₂)₅] and II (R = H, Me, MeO, R¹ = H, n = 1; R = R¹ = H, n = 2) gave 68-80% III (R, R¹, R² as before) and 64-78% pyrazolopyridone IV (R, R¹, n as before), resp. Reaction of I [R = Me, R¹ = H, R² = 4-R³C₆H₄, R³ = H, Me, MeO, Cl, Br; R = Me, R¹R² = (CH₂)₃, (CH₂)₄] and II (R = Me, R¹ = H, n = 1) with guanidine in the presence of 2 mol of NaOEt gave 31-71% pyridopyrimidinone V (R, R¹, R² as before) and 41% pyrimidoquinolinone VI.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 57663-05-5. 57663-05-5 belongs to nitriles-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Tetrahydropyrimidins, name is 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile, and the molecular formula is C8H8N2OS, HPLC of Formula: 57663-05-5.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Rastogi, Roopa R. published the artcileNovel method for the synthesis of substituted and fused 3-cyano-4-(methylmercapto)-2(1H)-pyridones using α-oxoketene S,S-diacetals, Synthetic Route of 57663-05-5, the publication is Journal of the Chemical Society, Chemical Communications (1975), 645, database is CAplus.

RCOCH:C(SMe)2 (R = Me, p-MeC6H4, 3-pyridyl) with cyanoacetamide and Me2CHONa in refluxing Me2CHOH gave 65-85% pyridone I. Similar reaction of the cycloalkanones II (n = 1 and 2) and III gave 77% pyrindinone IV (n = 1), 76% quinolinone IV (n = 2), and 65% benzoquinoline V.

Journal of the Chemical Society, Chemical Communications published new progress about 57663-05-5. 57663-05-5 belongs to nitriles-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Tetrahydropyrimidins, name is 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile, and the molecular formula is C8H8N2OS, Synthetic Route of 57663-05-5.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Taylor, Edward C. published the artcilePteridines. XXXIV. Synthesis of 8-hydroxy-7(8H)-pteridinones (pteridine hydroxamic acids), Formula: C10H11N3O3S, the publication is Journal of Organic Chemistry (1975), 40(16), 2332-6, database is CAplus and MEDLINE.

A series of 2,4-diamino-6-alkyl-substituted 8-hydroxy-7(8H)-pteridinones (pteridinehydroxamic acids) (I) was prepared from 2,4-diamino-6-substituted pteridine 8-oxides by chlorination in glacial AcOH, followed by cleavage of the resulting pteridinehydroxamic acid anhydrides II with ethanolic HCl. An alternative but less satisfactory route to 2,4-diamino-6-methyl-8-hydroxy-7(8H)-pteridinone involved condensation of pyruvohydroxamoyl chloride with aminomalononitrile tosylate to give 2-amino-3-cyano-5-methyl-6-chloropyrazine 1-oxide, hydrolysis to the pyrazinehydroxamic acid III, and cyclization with guanidine.

Journal of Organic Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C12H15ClO3, Formula: C10H11N3O3S.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts