Month: December 2022

Li, Zhenyu published the artcileSynthesis and anti-HIV evaluation of novel 1,2,4-triazole derivatives as potential non-nucleoside HIV-1 reverse transcriptase inhibitors, Name: 2-(Chloromethyl)benzonitrile, the publication is Letters in Drug Design & Discovery (2013), 10(1), 27-34, database is CAplus.

A series of novel 1,2,4-triazole derivatives was designed and synthesized. All of the new compounds were evaluated for their anti-HIV activities in MT-4 cells. Three of them showed moderate activities against wild-type HIV-1 with an EC₅₀ of 17.4-4.87 μM. Among the active compounds, 3-{[4-(3,4-dimethoxybenzylidenamino)-5-(furan-2-yl)-4H-1,2,4-triazol-3-ylthio]methyl}benzonitrile was identified as the promising compound (EC₅₀ = 17.4 μM, SI = 13). However, no compound displayed inhibitory activity against HIV-2.

Letters in Drug Design & Discovery 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, Name: 2-(Chloromethyl)benzonitrile.

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

Zeng, Yanqun published the artcileDesign and synthesis of piperidine derivatives as novel human heat shock protein 70 inhibitors for the treatment of drug-resistant tumors, Recommanded Product: 2-(Chloromethyl)benzonitrile, the publication is European Journal of Medicinal Chemistry (2015), 19-31, database is CAplus and MEDLINE.

HSP70 is a potential target for tumor treatment. HSP70 plays significant roles in several biol. processes, including the regulation of apoptosis. In this study, piperidine derivatives were designed as novel HSP70 inhibitors based on virtual fragment screening performed in Dock 4.0, Discovery Studio 2.5 and SYBYL 6.9. A total of 67 novel piperidine derivatives were synthesized. Cell viability assays were performed in 16 cancer cell lines. The emphasis was placed on lapatinib-resistant breast cancer cells (BT/Lap^R1.0, MDA-MB-361, SK/Lap^R1.0, and MDA-MB-453). The compounds I [R = 4-NCC₆H₄, 2-Cl-4-FC₆H₃, 2,4-Cl₂C₆H₃, 4-MeC₆H₄, 2-ClC₆H₄] significantly inhibited the proliferation of human breast cancer cells. Compound I [R = 4-NCC₆H₄] (II) inhibited the growth of BT474 and BT/Lap^R1.0 cells with IC₅₀ values of 1.41 μM and 1.47 μM, resp. The binding affinity of II/HSP70 was evaluated by surface plasmon resonance and yielded K_d values of 2.46 μM. The LD₅₀ was 869.0 mgkg^-1. These data suggest that II may be a potential candidate compound for tumor treatment.

European Journal of Medicinal Chemistry 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 C8H7NaO4S, Recommanded Product: 2-(Chloromethyl)benzonitrile.

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

Zhang, Wenjun published the artcilePalladium-catalyzed Aminocarbonylation of Benzylic Chlorides Using Carbamoylsilane as an Amide Source: Efficient Access of Secondary Aryl Acetamides, Formula: C8H6ClN, the publication is Current Organic Synthesis (2017), 14(7), 1067-1072, database is CAplus.

A novel and highly efficient synthetic method toward secondary arylacetamides RCH₂C(O)N(CH₃)CH₂OCH₃ (R = Ph, 3,4-Cl₂C₆H₃, C₆H₅CH=CH, naphth-1-yl, etc.) by palladium-catalyzed aminocarbonylation of aryl halides RCH₂Cl was developed using N-methoxymethyl-N-methylcarbamoyl(trimethyl)silane as amide source. The methoxymethyl group was used as an amino protecting group and can be easily hydrolyzed in acid condition to afford secondary arylacetamides RCH₂C(O)NHCH₃ . The scope and limitation of the aminocarbonylation were investigated. The relative position of substituent on the aryl ring is used to influence on this transformation. In this protocol, the methoxymethyl group was used as an amino protecting group and can be easily hydrolyzed.

Current Organic Synthesis 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 C10H12O5, Formula: C8H6ClN.

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

Stuckey, Jacob I. published the artcileIdentification and characterization of second-generation EZH2 inhibitors with extended residence times and improved biological activity, Product Details of C8H8N2OS, the publication is Journal of Biological Chemistry (2021), 100349, database is CAplus and MEDLINE.

Kinetic methodologies for studying EZH2-inhibitor-binding kinetics that had allowed to identify a unique structural modification that results in significant increases in the drug-target residence times of all EZH2 inhibitor scaffolds was studied. The unexpected residence time enhancement bestowed by this modification had enabled us to create a series of second-generation EZH2 inhibitors with sub-pM binding affinities. Both biophys. evidence validating this sub-pM potency and biol. evidence demonstrating the utility and relevance of such high-affinity interactions with EZH2 was provided.

Journal of Biological Chemistry 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 C12H10F2Si, Product Details of C8H8N2OS.

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

Lin, Kuaile published the artcileSynthesis and biological evaluation of xanthine derivatives on dipeptidyl peptidase 4, Formula: C8H6ClN, the publication is Chemical & Pharmaceutical Bulletin (2013), 61(4), 477-482, database is CAplus and MEDLINE.

A series of xanthine derivatives in which a methylene was inserted at position eight of xanthine scaffold was synthesized and evaluated as inhibitors of dipeptidyl peptidase 4 (DPP-4) for the treatment of type 2 diabetes. As a results of a structure-activity relationship (SAR) study of the series, the compounds with 4-methyl-quinazoline-2-yl-Me group at N-1 position and 2-aminoethylaminomethyl group displayed better antidiabetic activity. Two compounds inhibited DPP-4 and displayed a more than 100-fold selectivity over DPP-7 and DPP-8. The title compounds thus formed included a xanthine derivative (I) and related substances, such as 8-[(3R)-3-amino-1-piperidinyl]-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-1H-purine-2,6-dione (linagliptin) and analogs, such as 2,2′-[[8-[(3R)-3-amino-1-piperidinyl]-3,6-dihydro-3-methyl-2,6-dioxo-1H-purine-1,7(2H)-diyl]bis(methylene)]bis[benzonitrile]. The synthesis of the target compounds was achieved using 3,9-dihydro-8-(hydroxymethyl)-3-methyl-1H-purine-2,6-dione as a key intermediate.

Chemical & Pharmaceutical 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

Zhang, Zhi-Jun published the artcileCharacterization of a new nitrilase from Hoeflea phototrophica DFL-43 for a two-step one-pot synthesis of (S)-β-amino acids, Formula: C8H6ClNO, the publication is Applied Microbiology and Biotechnology (2018), 102(14), 6047-6056, database is CAplus and MEDLINE.

A nitrilase from Hoeflea phototrophica DFL-43 (HpN) demonstrating excellent catalytic activity towards benzoylacetonitrile was identified from a nitrilase tool-box, which was developed previously in our laboratory for (R)-o-chloromandelic acid synthesis from o-chloromandelonitrile. The HpN was overexpressed in Escherichia coli BL21 (DE3), purified to homogeneity by nickel column affinity chromatog., and its biochem. properties were studied. The HpN was very stable at 30-40°C, and highly active over a wide range of pH values (pH 6.0-10.0). In addition, the HpN could tolerate against several hydrophilic organic solvents. Steady-state kinetics indicated that HpN was highly active towards benzoylacetonitrile, giving a K_M of 4.2 mM and a k_cat of 170 s^-1, the latter of which is ca. fivefold higher than the highest record reported so far. A cascade reaction for the synthesis of optically pure (S)-β-phenylalanine from benzoylacetonitrile was developed by coupling HpN with an ω-transaminase from Polaromonas sp. JS666 in toluene-water biphasic reaction system using β-alanine as an amino donor. Various (S)-β-amino acids could be produced from benzoylacetonitrile derivatives with moderate to high conversions (73-99%) and excellent enantioselectivity (> 99% ee). These results are significantly advantageous over previous studies, indicating a great potential of this cascade reaction for the practical synthesis of (S)-β-phenylalanine in the future.

Applied Microbiology and Biotechnology 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 C14H26O2, Formula: C8H6ClNO.

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

Zhang, Sheng published the artcilePalladium-Catalyzed sp²-sp³ Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes, Category: nitriles-buliding-blocks, the publication is Journal of Organic Chemistry (2017), 82(11), 5974-5980, database is CAplus and MEDLINE.

Palladium-catalyzed remote sp²-sp³ coupling reaction of chloromethylarenes with allyltrimethoxysilane is described in this work. The allylation reaction regioselectively occurred on the para-positions of 1-(chloromethyl)naphthalenes and benzyl chlorides to form new C(sp²)-C(sp³) bonds. The reaction proceeds smoothly under mild conditions to produce allyl arenes in moderate to excellent yields.

Journal of Organic Chemistry 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 C7H5Cl2NO, Category: nitriles-buliding-blocks.

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

Lubov, Dmitry P. published the artcilePalladium-Aminopyridine Catalyzed C-H Oxygenation: Probing the Nature of Metal Based Oxidant, HPLC of Formula: 68569-14-2, the publication is ChemCatChem (2021), 13(24), 5109-5120, database is CAplus.

A mechanistic study of direct selective oxidation of benzylic C(sp³)-H groups with peracetic acid, catalyzed by palladium complexes with tripodal amino-tris(pyriylmethyl) ligands, is presented. The oxidation of arylalkanes having secondary and tertiary benzylic C-H groups, predominantly yields, depending on the substrate and conditions, either the corresponding ketones or alcs. One of the three 2-pyridylmethyl moieties, which is pending in the starting catalyst, apparently, facilitates the active species formation and takes part in stabilization of the high-valent Pd center in the active species, occupying the axial coordination site of palladium. The catalytic, as well as isotopic labeling experiments, in combination with ESI-MS data and DFT calculations, point out palladium oxyl species as possible catalytically active sites, operating essentially via C-H abstraction/oxygen rebound pathway. For the ketones formation, O-H abstraction/β-scission mechanism has been proposed.

ChemCatChem published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, HPLC of Formula: 68569-14-2.

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

Sathyamoorthi, Govindarao published the artcileLaser active cyanopyrromethene-BF₂ complexes, Product Details of C7H8N2, the publication is Heteroatom Chemistry (1994), 5(4), 403-7, database is CAplus.

Treatment with a mixture of formic and hydrobromic acids converted Et 3,4-diethyl-5-methylpyrrole-2-carboxylate to 3,3,’,4,4′-tetraethyl-5,5′-dimethylpyrromethene hydrobromide presumably via the condensation of α-unsubstituted and α-formylpyrrole intermediates formed in situ. The corresponding 6-cyanohexaalkylpyrromethane was obtained by the addition of hydrogen cyanide to the pyrromethene and was oxidized with bromine to an unstable pyrromethene, an intermediate converted to 1,2,6,7-tetraethyl-3,5-dimethyl-8-cyanopyrromethene-BF₂ complex(PM-TEDC), λ_las (plastic) 613-639 nm, in a reaction with boron trifluoride etherate. Et 3,4,5-trimethylpyrrole-2-carboxylate was similarly converted to 1,2,3,5,6,7-hexamethyl-8-cyanopyrromethene-BF₂ complex, (PM-HMC), λ_las (plastic) 615-639 nm. Immediately after formation by a condensation between propionyl chloride and 2,4-dimethyl-3-cyanopyrrole, unstable 3,3′,5,5′-tetramethyl-6-ethyl-4,4′-dicyanopyrromethene hydrochloride was treated with boron trifluoride etherate to give 1,3,5,7-tetramethyl-2,6-dicyano-8-ethylpyrromethene-BF₂ complex, λ_las (ethanol) 540-565 nm.

Heteroatom Chemistry published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Product Details of C7H8N2.

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

Nazari, S. Hadi published the artcileNickel-Catalyzed Suzuki Cross Couplings with Unprotected Allylic Alcohols Enabled by Bidentate N-Heterocyclic Carbene (NHC)/Phosphine Ligands, HPLC of Formula: 214360-44-8, the publication is ACS Catalysis (2018), 8(1), 86-89, database is CAplus.

Cross couplings between simple allylic alcs. and aryl and vinyl boronic acids are efficiently catalyzed by nickel(0) catalysts and bidentate N-heterocyclic carbene/phosphine ligands. The bidentate nature of the ligand is shown to extend catalyst lifetime and enable high yields of the corresponding cross-coupling products. X-ray crystallog. confirms the bidentate nature of the ligand scaffold. Multistep cross coupling-alkene/alkyne insertions reactions are also conducted and the bidentate nature of the substrate makes the pendant phosphine of the ligand unnecessary.

ACS Catalysis published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, HPLC of Formula: 214360-44-8.

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