Author: Jessica.F

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

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

Gadd, Adam J. R. published the artcileHigh potency of lipid conjugated TLR7 agonist requires nanoparticulate or liposomal formulation, COA of Formula: C13H7Cl2N5, the publication is European Journal of Pharmaceutical Sciences (2018), 268-276, database is CAplus and MEDLINE.

Here, we studied the effect of formulation on potency of a 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine (DOPE) conjugated TLR7 agonist (DOPE-TLR7a) alongside assessing phys. form using Dynamic Light Scattering (DLS), Nanosight Particle Tracking (NTA) anal. and Small Angle X-ray Scattering (SAXS). A very high potency of DOPE-TLR7a conjugate (EC₅₀ around 9 nM) was observed either when prepared by direct dilution from DMSO or when formulated into 400-700 nm large multilamella liposomes containing dimethyldioctadecylammonium bromide salt (DDA) and DOPE. When prepared by dissolution in DMSO followed by dilution in aqueous culture medium, 93 ± 5 nm nanoparticles were formed. Without dilution from solution in DMSO, no nanoparticles were observed and no immunostimulatory activity could be detected without this formulation step. SAXS anal. of the conjugate after DMSO dissolution/water dilution revealed a lamellar order with a layer spacing of 68.7 Å, which correlates with arrangement in groups of 3 bilayers. The addition of another immunostimulatory glycolipid, trehalose-6,6-dibehenate (TDB), to DOPE:DDA liposomes gave no further increase in immunostimulatory activity beyond that provided by incorporating DOPE-TLR7a. Given the importance of nanoparticle or liposomal formulation for activity, we conclude that the major mechanism for increased potency when TLR7 agonists are conjugated to macromols. is through alteration of phys. form.

European Journal of Pharmaceutical Sciences published new progress about 115204-76-7. 115204-76-7 belongs to nitriles-buliding-blocks, auxiliary class 5.6_Aromatics,Purines, name is 4-((2,6-Dichloro-9H-purin-9-yl)methyl)benzonitrile, and the molecular formula is C13H7Cl2N5, COA of Formula: C13H7Cl2N5.

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

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