Month: February 2023

Fragment-Based Approach to the Development of an Orally Bioavailable Lactam Inhibitor of Lipoprotein-Associated Phospholipase A2 (Lp-PLA₂) was written by Woolford, Alison J.-A.;Day, Philip J.;Beneton, Veronique;Berdini, Valerio;Coyle, Joseph E.;Dudit, Yann;Grondin, Pascal;Huet, Pascal;Lee, Lydia Y. W.;Manas, Eric S.;McMenamin, Rachel L.;Murray, Christopher W.;Page, Lee W.;Patel, Vipulkumar K.;Potvain, Florent;Rich, Sharna J.;Sang, Yingxia;Somers, Don O.;Trottet, Lionel;Wan, Zehong;Zhang, Xiaomin. And the article was included in Journal of Medicinal Chemistry in 2016.Related Products of 104798-53-0 This article mentions the following:

Lp-PLA₂ has been explored as a target for a number of inflammation associated diseases, including cardiovascular disease and dementia. This article describes the discovery of a new fragment derived chemotype that interacts with the active site of Lp-PLA₂. The starting fragment hit was discovered through an x-ray fragment screen and showed no activity in the bioassay (IC₅₀ > 1 mM). The fragment hit was optimized using a variety of structure-based drug design techniques, including virtual screening, fragment merging, and improvement of shape complementarity. A novel series of Lp-PLA₂ inhibitors was generated with low lipophilicity and a promising pharmacokinetic profile. In the experiment, the researchers used many compounds, for example, 2-Fluoro-5-hydroxybenzenecarbonitrile (cas: 104798-53-0Related Products of 104798-53-0).

2-Fluoro-5-hydroxybenzenecarbonitrile (cas: 104798-53-0) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Related Products of 104798-53-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Amphiphilic allylation of activated alkenes by allyl acetates and allylstannanes catalyzed by palladium nanoparticles: an easy access to stereodefined substituted cyclohexene derivatives was written by Adak, Laksmikanta;Bhadra, Sukalyan;Chattopadhyay, Kalicharan;Ranu, Brindaban C.. And the article was included in New Journal of Chemistry in 2011.Recommanded Product: 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

An efficient vicinal double allylation of activated alkenes by allyl acetates and allylstannanes catalyzed by palladium nanoparticles, generated in situ from palladium(ii) chloride, has been demonstrated. Several activated alkenes produce functionalized 1,7-octadiene derivatives in one pot. The additions of substituted allyl acetates are highly regioselective. The Grubbs cyclization of octadiene derivatives gives an easy access to stereodefined substituted cyclohexene derivatives In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Recommanded Product: 2-(Anthracen-9-ylmethylene)malononitrile).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Recommanded Product: 2-(Anthracen-9-ylmethylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A strategy of two-step tandem catalysis towards direct N-alkylation of nitroarenes with ethanol via facile fabricated novel Co-based catalysts derived from coordination polymers was written by Wang, Jing;Qi, Tianqinji;Li, Zhibin;She, Wei;Li, Xuewei;Li, Jingfang;Yan, Pengfei;Li, Weizuo;Li, Guangming. And the article was included in Journal of Catalysis in 2019.Computed Properties of C9H10N2 This article mentions the following:

Three novel N-doped carbon supported Co/Co₃O₄ catalysts, namely, Co@CN-hmta, Co@CN-larg and Co-Co₃O₄@CN-bipy, with sheet-, worm-, honeycomb-like morphologies resp., have been fabricated by the pyrolysis of well-defined coordination polymers (CPs). Base upon the application of as-prepared catalysts, for the reaction of N-alkylation of nitroarenes 4-RC₆H₄NO₂ (R = H, 3-Cl, 4-Me, etc.) with ethanol, a direct two-step tandem reaction is realized, in which Co@CN-hmta delivers 100% conversion/selectivity of N-ethylaniline/N,N-diethylaniline from the direct N-alkylation of nitroarenes with ethanol. The kinetic studies were conducted to confirm that the N-alkylation of aniline with ethanol is the rate-determining step in the two-step tandem reaction. The SEM/EDX, XRD, Raman, TEM, XPS, and CO₂-TPD characterization results have revealed that sizes and dispersion of metallic Co, amount of structural defects and surface Lewis basicity towards three catalysts can be tuned by changing the structures of Co-based CPs designed by different organic linkers, which may also help to understand the preparation of industrial catalysts on a mol. level. The optimized Co@CN-hmta catalyst is easily recycled by using the external magnet for successive reuses without any loss in both activity and selectivity. This is the first reported carbon-nitrogen species supported Co/Co₃O₄ catalysts derived from the CPs, which could effectively catalyze the N-alkylation of nitroarenes with ethanol to produce the secondary amines and/or tertiary amines. This low-cost, recyclable and easy scale-up N-doped carbon supported catalyst may be of potential application in various heterogeneous catalytic reactions. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Computed Properties of C9H10N2).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Computed Properties of C9H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery of Novel Indazoles as Potent and Selective PI3Kδ Inhibitors with High Efficacy for Treatment of Hepatocellular Carcinoma was written by Qi, Jifeng;Wang, Weihua;Tang, Yongmei;Lou, Shengying;Wang, Jiaer;Yuan, Tao;He, Qiaojun;Yang, Bo;Zhu, Hong;Cui, Sunliang. And the article was included in Journal of Medicinal Chemistry in 2022.Category: nitriles-buliding-blocks This article mentions the following:

A total of 26 indazole derivatives I (R¹ = H, F, Cl, CF₃; R² = H, F, Me; R³ = Me, Et, isopropyl; R⁴ = pyridin-3-yl, 3,5-difluorophenyl, 4-cyanophenyl, etc.; R⁵ = 9H-purin-6-yl, 2-amino-9H-purin-6-yl, 3-cyanopyridin-2-yl, etc.) were designed and prepared to identify a novel compound I (R¹ = Cl; R² = H; R³ = methyl; R⁴ = pyridin-3-yl; R⁵ = 2,6-diamino-5-cyanopyrimidin-4-yl) (II) with good isoform selectivity, PK profile, and potency. Compared to Idelalisib and Sorafenib, the pharmacodynamic (PD) studies showed that II exhibits superior efficacy in HCC cell lines and xenograft models, and the mechanistic study showed that II robustly suppresses the downstream AKT pathway to induce subsequent apoptotic cell death in HCC models. Therefore, this work provides a new structural design of PI3Kδ inhibitors for a novel and efficient therapeutic small mol. toward HCC. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Category: nitriles-buliding-blocks).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of 3-cyanocoumarins was written by Czerney, P.;Hartmann, H.. And the article was included in Journal fuer Praktische Chemie (Leipzig) in 1981.Electric Literature of C14H14N2O2 This article mentions the following:

The cyanocoumarins I (R = H, 6-Br, 8-MeO, 7-Me₂N, 7-Et₂N, 7-pyrrolidino, 5,6-benzo) were prepared by cyclization of the benzaldehydes II with H₂NCOCH₂CN to give the coumarincarboxamides III, which were treated with POCl₃-DMF and then hydrolyzed. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Electric Literature of C14H14N2O2).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Electric Literature of C14H14N2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some thienyl analogs of amidinomycin was written by Paul, Heinz;Migulla, Heinz. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 1978.Name: 4-Nitrothiophene-2-carbonitrile This article mentions the following:

RCONHCH₂CH₂CN (I; R = 4-nitro-2-thienyl, 5-nitro-2-thienyl, 2-thienyl) were prepared by saponification of RCN, chlorination of RCO₂H, and reaction of RCOCl with H₂NCH₂CH₂CN. I [R = 4-(4-tosylamino)-2-thienyl, 4-amino-2-thienyl, 5-amino-2-thienyl, 4-isopropylamino-2-thienyl, 5-isoproipylamino-2-thienyl] were similarly prepared I were subjected to ethanolysis to give RCONHCH₂CH₂C(:NH)OEt, which were treated with NH₃ to give amidines RCONHCH₂CH₂C(:NH)NH₂. None of the compounds prepared had any antiviral activity. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Name: 4-Nitrothiophene-2-carbonitrile).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Name: 4-Nitrothiophene-2-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Palladium(II)-Catalyzed Three-Component Tandem Cyclization Reaction for the One-Pot Assembly of 4-Arylquinazolines was written by Wang, Zijuan;Chen, Wenteng;He, Chang;Zhang, Guolin;Yu, Yongping. And the article was included in Synthesis in 2021.Synthetic Route of C7H5ClN2 This article mentions the following:

A one-pot method for joining three sep. components leading to an assortment of 4-arylquinazolines I (R¹ = H, 6-Cl, 7-Cl, 8-Cl, 6-Me, 6-Br; R² = H, Me, Ph; R³ = C₆H₅, 4-ClC₆H₄, 4-CH₃C₆H₄, etc.) in good to excellent yields is described. The method consists of a palladium(II)-catalyzed cascade reaction involving C(sp)-C(sp²) coupling followed by intramol. C-N bond formation. The reaction was readily scaled up to gram quantity and successfully applied to the synthesis of a translocator protein (TSPO) ligand II. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Synthetic Route of C7H5ClN2).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Synthetic Route of C7H5ClN2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

BF₃·Et₂O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant was written by Luo, Zhenli;Pan, Yixiao;Yao, Zhen;Yang, Ji;Zhang, Xin;Liu, Xintong;Xu, Lijin;Fan, Qing-Hua. And the article was included in Green Chemistry in 2021.Application of 10282-32-3 This article mentions the following:

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF₃·Et₂O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug mols. and biol. relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atm. or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF₃ and hydride transfer from formic acid. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Application of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Application of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A Metalloligand Appended with Thiazole Rings: Heterometallic {Co³⁺-Zn²⁺} and {Co³⁺-Cd²⁺} Complexes and Their Heterogeneous Catalytic Applications was written by Bansal, Deepak;Hundal, Geeta;Gupta, Rajeev. And the article was included in European Journal of Inorganic Chemistry in 2015.Computed Properties of C18H10N2 This article mentions the following:

This work describes a Co³⁺-based metalloligand containing appended thiazole rings and its reactions with secondary metal ions to produce heterometallic {Co³⁺-Zn²⁺} and {Co³⁺-Cd²⁺} complexes. Structural studies show that some of the appended thiazole rings from the metalloligand coordinate to secondary metal ions, whereas the remaining ones act as hydrogen-bond acceptors to metal-bound CH₃OH or H₂O mols. These heterometallic complexes function as reusable heterogeneous catalysts for the ring-opening reactions of epoxides as well as cyanation and Knoevenagel condensation reactions of aldehydes. The catalytic results illustrate that the microenvironment remains intact during the catalysis and potentially enhances the substrate interaction with the Lewis acidic secondary metal ions. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Computed Properties of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ir(III)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles was written by Kim, Youyoung;Kim, Dongwook;Chang, Sukbok. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.Safety of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

An iridium(III)-catalyzed electrooxidative intramol. dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines was described. The developed method allowed the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggested that the reaction proceeds through the electro-oxidation induced reductive elimination pathway. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Safety of 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Safety of 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts