Category: nitriles-buliding-blocks

Zhang, Hong-Jian published the artcileSynthesis and pharmacological evaluation of new 3,4-dihydroisoquinolin derivatives containing heterocycle as potential anticonvulsant agents, Formula: C8H6ClN, the publication is Molecules (2016), 21(12), 1635-1650, database is CAplus and MEDLINE.

Novel, fused 3,4-dihydroisoquinolines I (R¹ = H, Me, n-C₅H₁₁, etc.) and II [R² = n-C₆H₁₃ (III), n-C₇H₁₅, n-C₈H₁₇, PhCH₂, 4-ClC₆H₄CH₂] were synthesized and evaluated for their anticonvulsant activity using maximal electroshock (MES) test and pentylenetetrazole (PTZ)-induced seizure test. Among them, compound III showed significant anticonvulsant activity in MES tests with an ED₅₀ value of 63.31 mg/kg and it showed wide margins of safety with protective index (PI > 7.9). Compound III showed much higher anticonvulsant activity than that of valproate. Compound III also demonstrated potent activity against PTZ-induced seizures. A docking study of compound III in the benzodiazepine (BZD)-binding site of γ-aminobutyric acid_A (GABA_A) receptor confirmed possible binding of compound with the BZD receptors.

Molecules 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 C5H7NO, Formula: C8H6ClN.

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

Kalugin, V. E. published the artcileSynthesis of derivatives of pyrido[3′,2′:4,5]furo[3,2-c]isoquinoline heterocyclic system, Computed Properties of 612-13-5, the publication is Russian Chemical Bulletin (2014), 63(2), 426-430, database is CAplus.

An approach to the synthesis of derivatives of new heterocyclic system, pyrido[3′,2′:4,5]-furo[3,2-c]isoquinoline I [R = R¹= Me; R = Ph, R¹ = 4-MeC₆H₄, 2-thienyl; R = CF₃, R¹ = Ph], was suggested. A condensation reaction of substituted 3-cyanopyridin-2(1H)-ones with Me 2-(chloromethyl)benzoate and subsequent treatment of the condensation product with potassium tert-butoxide leads to substituted pyrido[3′,2′:4,5]furo[3,2-c]-isoquinolin-5(6H)-ones. Similarly, a condensation reaction of substituted 3-cyanopyridin-2(1H)-ones with 2-(chloromethyl)benzonitrile and subsequent treatment of the condensation product with potassium tert-butoxide gives substituted 5-aminopyrido[3′,2′:4,5]furo[3,2-c]-isoquinolines II.

Russian Chemical Bulletin 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, Computed Properties of 612-13-5.

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

Kalugin, V. E. published the artcileSynthesis of substituted 5-aminobenzothieno[3,2-c]isoquinolines and their sulfinyl and sulfonyl derivatives, Category: nitriles-buliding-blocks, the publication is Russian Chemical Bulletin (2015), 64(4), 878-882, database is CAplus.

A method for the preparation of substituted 5-aminobenzothieno[3,2-c]isoquinolines I, (R = H, Me, Cl), in good yields by the condensation of substituted 2-mercaptobenzonitriles with 2-(chloromethyl)benzonitrile and a subsequent treatment of the condensation products with potassium tert-butoxide was suggested. The oxidation of the condensation products to sulfoxides or sulfones and a subsequent treatment of these compounds with potassium tert-butoxide led to the preparation of substituted 5-aminobenzothieno[3,2-c]isoquinoline 11-oxides or 5-aminobenzothieno[3,2-c]isoquinoline 11,11-dioxides in good yields.

Russian Chemical Bulletin 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, Category: nitriles-buliding-blocks.

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

Kalugin, V. E. published the artcileSynthesis of 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinoline derivatives from 3-cyanopyridine-2(1H)-thiones and 2-(chloromethyl)benzamide, Formula: C8H6ClN, the publication is Russian Chemical Bulletin (2018), 67(8), 1492-1499, database is CAplus.

Substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinolines were synthesized by condensation of substituted 3-cyanopyridine-2(1H)-thiones with 2-(chloromethyl)benzamide and subsequent treatment of the condensation products with potassium tert-butoxide. Oxidation of the condensation products to sulfoxides and sulfones followed by treatment of these compounds with potassium tert-butoxide gave substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinoline 11-oxides and substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinoline 11,11-dioxides in good yields.

Russian Chemical Bulletin 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, Formula: C8H6ClN.

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

Kalugin, V. E. published the artcileThe synthesis of 3-cyano-2-(organylamino)thieno[3,2-c]isoquinoline derivatives, Quality Control of 612-13-5, the publication is Russian Chemical Bulletin (2019), 68(3), 588-596, database is CAplus.

A method for the preparation of 3-cyano-2-(organylamino)thieno[3,2-c]isoquinoline derivatives was developed. Alkylation of (2,2-dicyano-1-organylaminovinyl)thiolates with Me 2-(chloromethyl)benzoate or N-substituted 2-(chloromethyl)benzamides with the subsequent treatment of the alkylation products with potassium tert-butoxide gave 3-cyano-2-(organylamino)thieno[3,2-c]isoquinolin-5(4H)-ones. In the case of utilization of (chloromethyl)benzonitrile in this synthesis, 5-amino-3-cyano-2-organylaminothieno[3,2-c]iso-quinolines were obtained.

Russian Chemical Bulletin 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, Quality Control of 612-13-5.

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

Kalugin, V. E. published the artcileThe synthesis of substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinolines and their sulfinyl and sulfonyl derivatives, Formula: C8H6ClN, the publication is Russian Chemical Bulletin (2018), 67(5), 902-911, database is CAplus.

5-Aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinolines were synthesized via alkylation of 3-cyanopyridine-2(1H)-thiones with 2-(chloromethyl)benzonitrile followed by treatment of the products with potassium tert-butoxide. The oxidation of the alkylated products to corresponding sulfoxides or sulfones followed by treatment with potassium tert-butoxide provided the corresponding 11-oxides or 11,11-dioxides.

Russian Chemical Bulletin 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, Formula: C8H6ClN.

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

Kalugin, Victor E. published the artcileA convenient synthesis of benzofuro[3,2-c]isoquinolines and naphtho[1′,2′:4,5]furo[3,2-c]isoquinolines, Product Details of C8H6ClN, the publication is Tetrahedron Letters (2011), 52(14), 1557-1560, database is CAplus.

A convenient method for the preparation of benzofuro[3,2-c]isoquinoline derivatives is described. The condensation reaction of Me 2-(chloromethyl)benzoate with substituted salicylonitriles (I) and intramol. cyclization of the resulting substituted Me 2-[(2-cyanobenzyl)oxy]benzoates using potassium tert-butoxide results in substituted benzofuro[3,2-c]isoquinolin-5(6H)-ones. The same sequence of reactions starting from 2-(chloromethyl)benzonitrile and I gave substituted 5-aminobenzofuro[3,2-c]isoquinolines. In addition, this method is useful for the synthesis of other heterocycles. For example, using 1-cyano-2-naphthol, instead of I, gives naphtho[1′,2′:4,5]furo[3,2-c]isoquinolines.

Tetrahedron Letters 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, Product Details of C8H6ClN.

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

Schiaffo, Charles E. published the artcileStructure-Activity Relationship Analysis of Imidazoquinolines with Toll-like Receptors 7 and 8 Selectivity and Enhanced Cytokine Induction, Category: nitriles-buliding-blocks, the publication is Journal of Medicinal Chemistry (2014), 57(2), 339-347, database is CAplus and MEDLINE.

Toll-like receptors 7 and 8 (TLRs) have emerged as key targets in the design of small mol. adjuvants and stimulants for use in immunotherapies. This study examines the structure-activity relationship of a series of C2- and N1-substituted C7-methoxy-carbonyl-imidazo-quinolines to gain insight to the structural basis to TLR-7 and -8 selective activity. The anal. is further applied to evaluate the induction of multiple cytokines, including IL-10, IL-12, IL-1β, TNF-α, IFN-α, and IFN-γ, using murine BMDCs and human PBMCs. The results show TLR-7/8 activity is correlated to the C2-alkyl chain length, with peak activity occurring for the Bu (TLR-7) and pentyl (TLR-8) derivatives A similar SAR is identified in the production of IL-1β, IL-12, and IFN-γ, which are shown to depend on both the C2-alkyl chain length and substitution to the N1-position. The compounds were also potent stimulators of IFN-α and IL-10 production but with less pronounced structure-based correlations.

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, Category: nitriles-buliding-blocks.

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

Xue, Ya-Ping published the artcileDesign of Nitrilases with Superior Activity and Enantioselectivity towards Sterically Hindered Nitrile by Protein Engineering, Product Details of C8H6ClNO, the publication is Advanced Synthesis & Catalysis (2015), 357(8), 1741-1750, database is CAplus.

The enantioselective hydrolysis of ortho-chloromandelonitrile with nitrilase is one of the most attractive approaches to prepare (R)-ortho-chloromandelic acid. To date, efforts to develop this nitrilase-mediated process were plagued by either insufficient ee_p (enantiomeric excess of product) or low activity due to the steric hindrance from the ortho-substituted substrate. To improve the nitrilase potential for producing (R)-ortho-chloromandelic acid, an enhancement of both activity and enantioselectivity towards sterically hindered nitriles would be highly desirable. Mol. docking of the (R)-ortho-chloromandelonitrile into the active site of wild-type 2A6 nitrilase (nitA) allowed the identification of proximal nitA active site residues. Several residues (52, 132, 189 and 190) were selected as targets for single and double point mutation to improve nitA activity and enantioselectivity towards ortho-chloromandelonitrile. Targeted mutagenesis yielded several nitA variants with superior activity and enantioselectivity. The best mutant T132A/F189T exhibited a 4.37-fold higher specific activity (7.39 U/mg) towards ortho-chloromandelonitrile than the wild-type nitA. More importantly, the enantioselectivity (E) was improved from 17.34 to >200, resulting in a highly enantiopure product. Mol. docking experiments further support the enhanced activity and enantioselectivity shown exptl. and the structural effects of this amino acid substitution on the active site of nitA are provided. The amino acids at sites 189 and 132 determine the activity and enantioselectivity towards ortho-chloromandelonitrile. With mutant T132A/F189T as a catalyst, a maximum of 450 mM of (R)-ortho-chloromandelic acid was produced with a 90% conversion and >99% ee_p within 3 h. This is the first time that a high productivity of (R)-ortho-chloromandelic acid of up to 671.76 g L^-1 d^-1 using a nitrilase-mediated approach is reported. The engineered T132A/F189T variant represents a promising and competitive biocatalyst for practical application in synthesizing (R)-ortho-chloromandelic acid.

Advanced Synthesis & Catalysis 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 C11H15NO2, Product Details of C8H6ClNO.

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

Yin, Shu-Qiang published the artcilePreparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(11), 3314-3319, database is CAplus and MEDLINE.

The small chem. compound 8-ethoxy-2-(4-fluorophenyl)-3-nitro-2H-chromene (S14161) was recently identified as an inhibitor of the phosphoinositide 3-kinase (PI3K). In the present study, the authors designed a novel synthesis of S14161 and prepared a series of its analogs via the oxa-Michael-Henry reaction in the presence of catalytic amounts of l-proline and triethylamine. Further structural simplification led to the identification of 6-bromo-8-ethoxy-3-nitro-2H-chromene (I, BENC-511) that exhibited potent antiproliferative activities against a panel of 12 tumor cell lines. Compared with S14161, BENC-511 was more potent in blocking the AKT phosphorylation and inducing cancer cell apoptosis. BENC-511 also displayed more potent effects on human umbilical vein epithelial cells (HUVEC) migration, suggesting its anti-angiogenesis activity.

Bioorganic & Medicinal Chemistry 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 C10H10O2, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

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