Tag: M.W=150-200

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

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

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

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

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

Ma, Zhuang published the artcileStable and reusable Ni-based nanoparticles for general and selective hydrogenation of nitriles to amines, Application In Synthesis of 238088-16-9, the publication is Chemical Science (2022), 13(36), 10914-10922, database is CAplus.

Silica supported ultrasmall Ni-nanoparticles allow for general and selective hydrogenation of all kinds of nitriles to primary amines under mild conditions. By calcination of a template material generated from Ni(II)nitrate and colloidal silica under air and subsequent reduction in the presence of mol. hydrogen the optimal catalyst was prepared The prepared supported nanoparticles are stable, was conveniently used and easily recycled. The applicability of the optimal catalyst material was shown by hydrogenation of >110 diverse aliphatic and aromatic nitriles including functionalized and industrially relevant substrates. Challenging heterocyclic nitriles, specifically cyanopyridines, provided the corresponding primary amines in good to excellent yields. The resulting amines serve as important precursors and intermediates for the preparation of numerous life science products and polymers.

Chemical Science published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C10H18BNO2, Application In Synthesis of 238088-16-9.

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

Mohlmann, Lennart published the artcileOrganocatalytic Enantioselective Synthesis of Tetrahydrofluoren-9-ones via Vinylogous Michael Addition/Henry Reaction Cascade of 1,3-Indandione-Derived Pronucleophiles, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2016), 18(4), 688-691, database is CAplus and MEDLINE.

An unprecedented organocatalytic enantioselective vinylogous Michael addition and Henry cyclization cascade is presented for the synthesis of highly substituted tetrahydrofluoren-9-ones employing novel 1,3-indandione-derived pronucleophiles and nitroalkenes. Following a very simple protocol, a wide range of products were obtained in good to excellent yields and with excellent enantioinduction (43-98% yields, up to 98% ee). The reaction proceeded with excellent diastereocontrol despite the simultaneous generation of four stereogenic centers. Surprisingly, when 2-(1-phenylethylidene)-1H-indandione was used as a pronucleophile, no cyclization was observed, and only Michael addition adducts were furnished in very good yields and excellent enantioselectivities.

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 C9H6N2O2, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Chang, Dan published the artcileMetal-Free Synthesis and Photophysical Properties of 1,2,4-Triarylpyrroles, HPLC of Formula: 5153-73-1, the publication is Journal of Organic Chemistry (2021), 86(1), 110-127, database is CAplus and MEDLINE.

A three-component reaction has been developed for the construction of multiaryl-substituted pyrrole derivatives from arylketones, amines, and nitrovinylarenes under metal-free conditions. Hence, homologous 1,2,4-triaryl-substituted pyrrole products were obtained in good to high yields. Furthermore, 2,3,5-triaryl-substituted pyrroles were selectively formed in the absence of nitrovinylarenes. The photophys. properties of some pyrrole products have been investigated to show good aggregation-induced emission (AIE) activity.

Journal of Organic 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, HPLC of Formula: 5153-73-1.

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

Hao, Feiyue published the artcileDirect Aziridination of Nitroalkenes Affording N-Alkyl-C-nitroaziridines and the Subsequent Lewis Acid Mediated Isomerization to β-Nitroenamines, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2017), 19(19), 5442-5445, database is CAplus and MEDLINE.

A mild and highly diastereoselective one-pot synthesis of trans-N-alkyl-C-nitroaziridines was achieved by treatment of nitroalkenes with aliphatic amines and N-chlorosuccinimide. Treatment of the obtained aziridines with a Lewis acid resulted in a facile ring opening reaction, accompanied by rearrangement and isomerization into functionalized (Z)-β-nitroenamines.

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 C9H6N2O2, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Sato, Takahiro published the artcileDiscovery of 3-(3-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole, FYX-051 – a xanthine oxidoreductase inhibitor for the treatment of hyperuricemia, HPLC of Formula: 135048-32-7, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(21), 6225-6229, database is CAplus and MEDLINE.

A previous study identified 2-[2-(2-methoxy-ethoxy)-ethoxy]-5-[5-(2-methyl-4-pyridyl)-1H-[1,2,4]triazol-3-yl]-benzonitrile as a safe and potent xanthine oxidoreductase (XOR) inhibitor for the treatment of hyperuricemia. A series of 3,5-dipyridyl-1,2,4-triazole derivatives were synthesized and their in vivo activity in lowering the serum uric acid levels in rats was examined As a result, 3-(3-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole (FYX-051) to be one of the most potent XOR inhibitors; it exhibited an extremely potent in vivo activity, weak CYP3A4-inhibitory activity and a better pharmacokinetic profile than the previously identified compound FYX-051 is currently being evaluated in a phase 2 clin. trial.

Bioorganic & Medicinal Chemistry Letters published new progress about 135048-32-7. 135048-32-7 belongs to nitriles-buliding-blocks, auxiliary class Pyridine,Nitrile,Hydrazine,Amine,Hydrazide,Amide, name is 2-Cyanoisonicotinohydrazide, and the molecular formula is C7H6N4O, HPLC of Formula: 135048-32-7.

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