Nitriles-buliding-blocks

Pharmacophore modeling, 3D-QSAR, synthesis, and anti-lung cancer evaluation of novel thieno[2,3-d][1,2,3]triazines targeting EGFR was written by Elrayess, Ranza;Abdel Aziz, Yasmine M.;Elgawish, Mohamed S.;Elewa, Marwa;Elshihawy, Hosam A.;Said, Mohamed M.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2020.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Two series of thieno[2,3-d][1,2,3]triazine derivatives were designed, synthesized, and biol. evaluated as potential epidermal growth factor receptor (EGFR) inhibitors targeting the non-small-cell lung cancer cell line H1299. Most of the synthesized compounds displayed IC₅₀ values ranging from 25 to 58 nM against H1299, which are superior to that of gefitinib (40μM). 3-(5,6,7,8-Tetrahydro-7H-cyclohexa[4:5]thieno[2,3-d]-1,2,3-triazin-4-ylamino)benzene-1,3-diamine (6b) achieved the highest cytotoxic activity against H1299 with an IC₅₀ value of 25 nM; it had the ability to decrease the EGFR concentration in H1299 cells from 7.22 to 2.67 pg/mL. In vitro, the IC₅₀ value of compound 6b was 0.33 nM against EGFR, which is superior to that of gefitinib at 1.9 nM and erlotinib at 4 nM. The three-dimensional quant. structure-activity relationships and mol. modeling studies revealed comparable binding modes of compound 6b, gefitinib, and erlotinib in the EGFR active site. The in silico ADME (absorption, distribution, metabolism, and excretion) prediction parameters of this compound revealed promising pharmacokinetic and physicochem. properties. Moreover, DFT (d. functional theory) calculations showed the high reactivity of compound 6b toward the EGFR compared with other compounds The designed compound 6b might serve as an encouraging lead compound for the discovery of promising anti-lung cancer agents targeting EGFR. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

ZIF-8 nanoparticles as an efficient and reusable catalyst for the Knoevenagel synthesis of cyanoacrylates and 3-cyanocoumarins was written by Kolmykov, Oleksii;Chebbat, Nassima;Commenge, Jean-Marc;Medjahdi, Ghouti;Schneider, Raphael. And the article was included in Tetrahedron Letters in 2016.Related Products of 51473-74-6 This article mentions the following:

Zeolitic imidazolate framework (ZIF-8) particles with an average size of ca. 355 nm and a sp. surface area of 1786 m².g^-1 were used as an heterogenous catalyst for the Knoevenagel synthesis of α,β-unsaturated cyanoesters and 3-cyanocoumarins. The preparation of 3-cyanocoumarins was efficiently achieved using DMF as the solvent and conducting the condensation at 80°. When the reaction was performed in ethanol, only the intermediates α,β-unsaturated cyanoesters were obtained. The ZIF-8 catalyst could be reused up to five times without any degradation in activity. SEM and XRD analyses demonstrated the high stability of ZIF-8 crystals during the recycling test. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Related Products of 51473-74-6).

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. 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.Related Products of 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Catalytic Asymmetric Addition of Organolithium Reagents to Aldehydes was written by Veguillas, Marcos;Sola, Ricard;Shaw, Luke;Macia, Beatriz. And the article was included in European Journal of Organic Chemistry in 2016.Related Products of 101219-69-6 This article mentions the following:

Herein we report an efficient catalytic system for the titanium-promoted enantioselective addition of organolithium reagents to aldehydes, based on chiral Ar-BINMOL ligands. Unprecedented yields and enantioselectivities are achieved in the alkylation reactions of aliphatic aldehydes. Remarkably, methyllithium can be added to a wide variety of aromatic and aliphatic aldehydes, providing versatile chiral Me carbinol units in a simple one-pot procedure under mild conditions and in very short reaction times. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Related Products of 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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.Related Products of 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Single-Crystalline, Size, and Orientation Controllable Nanowires and Ultralong Microwires of Organic Semiconductor with Strong Photoswitching Property was written by Jiang, Lang;Fu, Yanyan;Li, Hongxiang;Hu, Wenping. And the article was included in Journal of the American Chemical Society in 2008.COA of Formula: C18H10N2 This article mentions the following:

Single-crystalline, precise size-controlled nanowires and ultralong microwires with lengths reaching several millimeters of 2-anthracen-9-ylmethylenemalonitrile were prepared in large scale by cast assembly. The size and d. of the nanowires and microwires could be controlled by simply adjusting the concentration of the compound in casting solutions More importantly, the formation of these nanowires and microwires showed no substrate and solvent dependence and was orientation controllable. Highly reproducible and sensitive photoresponse characteristics were observed in these nanowires and microwires. Fast and reversible photoswitchers based on multiple or individual single-crystal microwires were fabricated via “multi times gold wire mask moving” technique with switch ratio over 100. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4COA of Formula: C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).COA of Formula: C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines was written by Fuwa, Haruhiko;Kobayashi, Toshitake;Tokitoh, Takashi;Torii, Yukiko;Natsugari, Hideaki. And the article was included in Synlett in 2004.Reference of 10282-32-3 This article mentions the following:

A novel intramol. nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-one derivatives induced by base treatment and its application to the expeditious synthesis of secondary aryl amines, including diaryl amines, are described. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Reference of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Reference of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tris(2-cyanoethyl)amine was written by Xu, An-Wu;Cai, Yue-Peng;Su, Cheng-Yong;Liu, Hong-Ke. And the article was included in Acta Crystallographica, Section C: Crystal Structure Communications in 2000.COA of Formula: C9H12N4 This article mentions the following:

In the title compound, N(CH₂CH₂CN)₃, (I), the three cyanoethyl groups adopt a conformation with the CN groups (I) oriented in the same direction, suggesting the compound may behave as a potential tripodal ligand. Crystallog. data are given. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1COA of Formula: C9H12N4).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.COA of Formula: C9H12N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

SAR study of 5-alkynyl substituted quinazolin-4(3H)-ones as phosphoinositide 3-kinase delta (PI3Kδ) inhibitors was written by Wei, Manman;Zhang, Xi;Wang, Xiang;Song, Zilan;Ding, Jian;Meng, Ling-Hua;Zhang, Ao. And the article was included in European Journal of Medicinal Chemistry in 2017.Electric Literature of C5H3ClN4 This article mentions the following:

PI3Kδ is a key component in the aberrant signaling transduction in B cell malignancy, therefore specific targeting PI3Kδ has become an attractive molecularly targeted therapy for chronic lymphocytic leukemia (CLL). Herein, we describe the discovery and optimization of a series of 5-alkynyl substituted PI3Kδ inhibitors based on the first FDA-approved inhibitor idelalisib. Compound 8d bearing the 1-morpholinohex-5-yn-1-one moiety as the C5-substituent was identified to have high potency against PI3Kδ (3.82 nM) and SU-DHL-6 cells (7.60 nM), resp. It was 154-fold selective over PI3Kα, 133-fold selective against PI3Kβ, and 24-fold selective against PI3Kγ. Treatment of MOLT-4 and SU-DHL-6 cells with compound 8d for 1 h resulted in reduction of phosphorylation of both Akt (S473) and its downstream S6k1 (T389) in a concentration-dependent manner. Compound 8d showed potent anti-proliferative activity as well against T lymphoblast MOLT-4, suggesting its potential activity in T-cell leukemia. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Electric Literature of C5H3ClN4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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. 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. Electric Literature of C5H3ClN4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ketene gem-dithiols; a convenient one-step procedure from aliphatic active methylenes: reactions and synthesis of polyfunctionally substituted thia- and azaheteroaromatics was written by Zayed, Salem E.. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 1996.Application of 58168-20-0 This article mentions the following:

It has been reported in the current literature that the isolation of certain ketene gem dithiols has failed due to dimerization. Generation of ketene gem-dithiols via trapping with other reactants led to formation of pyridine, pyrrole, pyridothiadiazole and pyrazolone derivatives In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Application of 58168-20-0).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Application of 58168-20-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nitriles in heterocyclic synthesis: novel routes to cyclopentenothienopyridines, cyclopentenothienopyrimidenes and cyclopentenopyrrolopyrazoles was written by Harb, Abdel Fattah Ali. And the article was included in Egyptian Journal of Pharmaceutical Sciences in 1992.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Aminocyclopentenothiophenecarbonitrile I prepared via an extension to the Gewald reaction, was converted into the cyclopentenothienopyridines II (R = H, NH₂) and III by treatment with acrylonitrile, malononitrile and Et cyanoacetate. I was converted into the corresponding cyclopentenothienopyrimidines IV (X = S, R¹ = NHPh; X = O, R¹ = Me, H) on treatment with Ph isothiocyanate, acetic anhydride and triethylorthoformate resp. Also the corresponding cyclopentenopyrrolopyrazole V was obtained by treating I with hydrazine hydrate. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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. Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rh^III– and Ir^III-catalyzed asymmetric transfer hydrogenation of ketones in water was written by Wu, Xiaofeng;Li, Xiaohong;Zanotti-Gerosa, Antonio;Pettman, Allan;Liu, Jianke;Mills, Allan James;Xiao, Jianliang. And the article was included in Chemistry – A European Journal in 2008.Recommanded Product: (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

Asym. transfer hydrogenation (ATH) of ketones by formate in neat water is shown to be viable with Rh-TsDPEN and Ir-TsDPEN catalysts, derived in situ from [Cp^*MCl₂]₂ (M = Rh, Ir) and TsDPEN. A variety of ketones were reduced, including non-functionalized aryl ketones, heteroaryl ketones, keto esters, and unsaturated ketones. In comparison with Ir-TsDPEN and the related Ru^II catalyst, the Rh^III catalyst is most efficient in water, affording enantioselectivities of up to 99% ee at substrate/catalyst (S/C) ratios of 100-1000 even without working under an inert atm. The aqueous phase reduction is shown to be highly pH-dependent; the optimum pH windows for TOF greater than 50 molmol^-1h^-1 for Rh- and Ir-TsDPEN are 5.5-10.0 and 6.5-8.5, resp. Outside the pH window, the reduction becomes slow or stagnant depending on the pH. However, the enantioselectivities erode only under acidic conditions. At a higher S/C ratio, the aqueous ATH by Rh-TsDPEN is shown to be product – as well as byproduct – inhibited; the product inhibition appears to stem at least partly from the reaction being reversible. The aqueous phase reduction is simple, efficient and environmentally benign, thus presenting a viable alternative for asym. reduction In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Recommanded Product: (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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. Recommanded Product: (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts