Tag: 100-200

Water-Soluble Hypervalent Iodine(III) Having an I-N Bond. A Reagent for the Synthesis of Indoles was written by Xia, Hai-Dong;Zhang, Yan-Dong;Wang, Yan-Hui;Zhang, Chi. And the article was included in Organic Letters in 2018.Name: 2-Amino-3-chlorobenzonitrile This article mentions the following:

A readily accessible and bench-stable water-soluble hypervalent iodine(III) reagent (phenyliodonio)sulfamate (PISA, PhI⁺NHSO₃^–) with an I-N bond was synthesized, and its structure was characterized by X-ray crystallog. anal. of its monoaqua complex. N-(Alkenylphenyl)amides such as I (R = Me, Et, BuCH₂, cyclopropyl, cyclohexyl, Ph, H, Et; R¹ = H, Me, n-Pr, PhCH₂) underwent regioselective rearrangement and oxidative cyclization mediated by PISA and H₂O in MeCN to yield acylindoles such as II (R = Me, Et, BuCH₂, cyclopropyl, cyclohexyl, Ph, H, Et; R¹ = H, Me, n-Pr, PhCH₂). Using this new method, the antiinflammatory agents indomethacin and zidometacin and 2-methylindole (an intermediate in the preparation of pravadoline) were prepared In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Name: 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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).Name: 2-Amino-3-chlorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery of a Potent, Selective, and Orally Available PI3Kδ Inhibitor for the Treatment of Inflammatory Diseases was written by Erra, Montse;Taltavull, Joan;Greco, Angelique;Bernal, Francisco Javier;Caturla, Juan Francisco;Gracia, Jordi;Dominguez, Maria;Sabate, Mar;Paris, Stephane;Soria, Salome;Hernandez, Begona;Armengol, Clara;Cabedo, Judit;Bravo, Monica;Calama, Elena;Miralpeix, Montserrat;Lehner, Martin D.. And the article was included in ACS Medicinal Chemistry Letters in 2017.Synthetic Route of C5H3ClN4 This article mentions the following:

The delta isoform of the phosphatidylinositol 3-kinase (PI3Kδ) has been shown to have an essential role in specific immune cell functions and thus represents a potential therapeutic target for autoimmune and inflammatory diseases. Herein, the optimization of a series of pyrrolotriazinones as potent and selective PI3Kδ inhibitors is described. The main challenge of the optimization process was to identify an orally available compound with a good pharmacokinetic profile in preclin. species that predicted a suitable dosing regimen in humans. Structure-activity relationships and structure-property relationships are discussed. This medicinal chem. exercise led to the identification of LAS191954 as a candidate for clin. development. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Synthetic Route of C5H3ClN4).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A convenient method for the α-carbethoxylation of alkylnitriles was written by Albarella, James Paul. And the article was included in Journal of Organic Chemistry in 1977.Name: 2-Cyclohexylacetonitrile This article mentions the following:

Treatment of RCH2CN (R = C3-16 alkyl) in THF at -78° with 2.3 molar equiv LiN(CHMe2)2 followed by 1.02-1.05 molar equiv (EtO)2CO or ClCO2Et gave excellent yields of the resp. RCH(CN)CO2Et. Similarly prepared were Et 2-cyano-2-cyclopentylacetate and the cyclohexyl analog. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Name: 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Name: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of Tertiary Benzylic Nitriles via Nickel-Catalyzed Markovnikov Hydrocyanation of α-Substituted Styrenes was written by Xing, Yidan;Yu, Rongrong;Fang, Xianjie. And the article was included in Organic Letters in 2020.Recommanded Product: 5351-07-5 This article mentions the following:

The Markovnikov hydrocyanation of α-substituted styrenes enables the synthesis of tertiary benzylic nitriles under nickel catalysis. The Lewis-acid-free transformation features an unprecedented functional groups tolerance, including the -OH and -NH₂ groups. A broad range of tertiary benzylic nitriles were obtained in good to excellent yields. In addition, an asym. version of this reaction was preliminarily investigated. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Recommanded Product: 5351-07-5).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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. 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.Recommanded Product: 5351-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Non-covalent thrombin inhibitors featuring P₃-heterocycles with P₁-monocyclic arginine surrogates was written by Reiner, John E.;Siev, Daniel V.;Araldi, Gian-Luca;Cui, Jingrong Jean;Ho, Jonathan Z.;Reddy, Komandla Malla;Mamedova, Lala;Vu, Phong H.;Lee, Kuen-Shan S.;Minami, Nathaniel K.;Gibson, Tony S.;Anderson, Susanne M.;Bradbury, Annette E.;Nolan, Thomas G.;Semple, J. Edward. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2002.Safety of 3-Amino-4-methylbenzonitrile This article mentions the following:

Investigations on P₂-P₃-heterocyclic dipeptide surrogates directed towards identification of an orally bioavailable thrombin inhibitor led us to pursue novel classes of achiral, non-covalent P₁-arginine derivatives The design, synthesis, and biol. activity of inhibitors NC1-NC30 that feature three classes of monocyclic P₁-arginine surrogates will be disclosed: (1) (hetero)aromatic amidines, amines and hydroxyamidines, (2) 2-aminopyrazines, and (3) 2-aminopyrimidines and 2-aminotetrahydropyrimidines. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Safety of 3-Amino-4-methylbenzonitrile).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. 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.Safety of 3-Amino-4-methylbenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and pharmacological study of 5,6,8,9-tetrahydro-4H,7H-pyrrolo[1,2-a]cyclopenta[b]thieno[3,2-f][1,4]diazepines was written by Vega, S.;Gil, M. Soledad;Darias, V.;Sanchez Mateo, Candelaria C.;Exposito, Maria A.. And the article was included in Pharmazie in 1995.SDS of cas: 70291-62-2 This article mentions the following:

The paper reports the synthesis of a series of 5,6,8,9-tetrahydro-4H,7H-pyrrolo[1,2-a]cyclopenta[b]thieno[3,2-f][1,4]diazepines and the results of the study on their CNS activity in mice. The pharmacol. properties of a previously prepared series of 5,6,7,8,9,10-hexahydrobenzo analogs is also described. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2SDS of cas: 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.SDS of cas: 70291-62-2

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

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

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

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