Month: January 2023

Syntheses of 2-chloro-4-acetylaminobenzonitrile isomers and structurally related compounds with biological activities was written by Grivsky, Eugene M.;Hitchings, George H.. And the article was included in Industrie Chimique Belge in 1974.Product Details of 53312-77-9 This article mentions the following:

Benzonitriles I, II, and III (Xn = 2-,3-Cl, 2-F, 2,6-, 2,4 -Cl2; NH2, NHCOR, NO2 in 2, 4, or 5 position; R = e.g., Me, H, CF3, CHCl2, CH2Cl, Et, Me2CH, Pr, CH:CHCO2H, CH2CH2CO2H) were prepared (5 I, 15 II and 88 III). E.g., reaction of 2,4-F-(O2N)C6H3CO2H with MeSO2NH2-PCl5 gave 96% I (Xn = 2-F, 4-NO2), which was reduced to give II (Xn = 2-F, 4-NH2), which was acetylated to give 95% III (Xn = 2-F, R = Me). III (Xn = 2-Cl, NHCOMe in 4 position) had LD50 (oral-mice)of 1800 mg/kg; and at 20 mg/kg (oral-mice) was an antide-pressant and at 25 and 50 mg kg (orally-rat), resp., was an anal-gesic and antipyretic. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Product Details of 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Product Details of 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Polymer-anchored Ru(II) complex as an efficient catalyst for the synthesis of primary amides from nitriles and of secondary amides from alcohols and amines was written by Islam, Sk Manirul;Ghosh, Kajari;Singha Roy, Anupam;Molla, Rostam Ali. And the article was included in Applied Organometallic Chemistry in 2014.Recommanded Product: 3-Methylthiophene-2-carbonitrile This article mentions the following:

A polymer-anchored ruthenium(II) catalyst was synthesized and characterized. Its catalytic activity was evaluated for the preparation of primary amides from aqueous hydration of nitriles in neutral condition. A range of nitriles were successfully converted to their corresponding amides in good to excellent yields. The catalyst was also effective in the preparation of secondary amides from the coupling of alcs. and amines. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Recommanded Product: 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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: 3-Methylthiophene-2-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis, anticancer activity and structure-activity relationship of some anticancer agents based on cyclopenta[b]thiophene scaffold was written by Said, Mohamed;Elshihawy, Hosam. And the article was included in Pakistan Journal of Pharmaceutical Sciences in 2014.COA of Formula: C8H8N2S This article mentions the following:

Methods for the synthesis of new heterocyclic systems of thieno[3,2-d]-1,2,3-triazine derivatives and N-3-cyano-5,6-dihydro-4H-cyclopenta[b]thiophene derivatives have been developed. The newly synthesized compounds were tested in vitro against human breast carcinoma cell line (MCF-7). Compounds N-(3-cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-2-[4-(pyrimidin-2-ylsulfamoyl)anilino]acetamide sodium salt and 4-(5,6-dihydro-7H-cyclopenta[4:5]thieno[2,3-d]-1,2,3-triazin-4-ylamino)phenol have shown the highest activity among the two synthesized series. The results of this study have led to the identification of two lead compounds with good inhibitory activities that can confirm the design of the next generation inhibitors of tyrosine kinase with fewer side effects such as hepatotoxicity and resistance. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2COA of Formula: C8H8N2S).

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. COA of Formula: C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A convenient synthesis of 3,3′,3”-triaminotripropylamine tetrahydrochloride-0.5 water was written by Laurino, John A.;Knapp, Spencer;Schugar, Harvey J.. And the article was included in Inorganic Chemistry in 1978.Product Details of 7528-78-1 This article mentions the following:

3,3′,3”-Iminotrispropionitrile I was converted to the title compound (II). Hydrogenation of I over Raney Ni (wet with Ac₂O) gave (AcNHCH₂CH₂CH₂)₃N which was hydrolyzed (aqueous HCl) to yield II. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Product Details of 7528-78-1).

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. 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.Product Details of 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design, Synthesis, and Biological Evaluation of Quinazolin-4-one-Based Hydroxamic Acids as Dual PI3K/HDAC Inhibitors was written by Thakur, Ashish;Tawa, Gregory J.;Henderson, Mark J.;Danchik, Carina;Liu, Suiyang;Shah, Pranav;Wang, Amy Q.;Dunn, Garrett;Kabir, Md.;Padilha, Elias C.;Xu, Xin;Simeonov, Anton;Kharbanda, Surender;Stone, Richard;Grewal, Gurmit. And the article was included in Journal of Medicinal Chemistry in 2020.Formula: C5H3ClN4 This article mentions the following:

A series of quinazolin-4-one based hydroxamic acids was rationally designed and synthesized as novel dual PI3K/HDAC inhibitors by incorporating an HDAC pharmacophore into a PI3K inhibitor (Idelalisib) via an optimized linker. Several of these dual inhibitors were highly potent (IC₅₀ < 10 nM) and selective against PI3Kγ, δ and HDAC6 enzymes and exhibited good antiproliferative activity against multiple cancer cell lines. The lead compound 48c, induced necrosis in several mutant and FLT3-resistant AML cell lines and primary blasts from AML patients, while showing no cytotoxicity against normal PBMCs, NIH3T3, and HEK293 cells. Target engagement of PI3Kδ and HDAC6 by 48c was demonstrated in MV411 cells using the cellular thermal shift assay (CETSA). Compound 48c showed good pharmacokinetics properties in mice via i.p. administration and provides a means to examine the biol. effects of inhibiting these two important enzymes with a single mol., either in vitro or in vivo. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Formula: C5H3ClN4).

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. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Formula: C5H3ClN4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

C-H chlorination of (hetero)anilines via photo/organo co-catalysis was written by Xie, Wuchen;Wang, Meng;Yang, Siyu;Chen, Yadong;Feng, Jie;Huang, Yatian. And the article was included in Organic & Biomolecular Chemistry in 2022.SDS of cas: 53312-77-9 This article mentions the following:

Herein, a photo-redox and organo co-catalyzed chlorination method for anilines to gave chloro-anilines ArNR¹R² [Ar = 4-ClC₆H₄, 3,4-di-Cl-5-FC₆H₂, 4-Cl-2,5-di-FC₆H₂, etc.; R¹ = H, Me; R² = H, Me, C(O)Me, Ph, pyrimidin-2-yl; R¹R² = (CH₂)₂N(CH₃)(CH₂)₂] was disclose. This method had great substrate generality and excellent mono-chlorination selectivity. Another merit of this method was the late-stage modification of drug mols., which would be useful in medicinal chem. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9SDS of cas: 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.SDS of cas: 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Thiophene/thiazole-benzene replacement on guanidine derivatives targeting α₂-Adrenoceptors was written by Flood, Aoife;Trujillo, Cristina;Sanchez-Sanz, Goar;Kelly, Brendan;Muguruza, Carolina;Callado, Luis F.;Rozas, Isabel. And the article was included in European Journal of Medicinal Chemistry in 2017.Reference of 70291-62-2 This article mentions the following:

Searching for improved antagonists of α₂-adrenoceptors, a thorough theor. study comparing the aromaticity of phenyl-, pyridinyl-, thiophenyl- and thiazolylguanidinium derivatives were carried out [at M06-2X/6-311++G(p,d) computational level] confirming that thiophene and thiazole were good ‘ring equivalent’ to benzene in these guanidinium systems. Based on these results, a small but chem. diverse library of guanidine derivatives were synthesized to explore the effect that the bioisosteric change has on affinity and activity at α₂-adrenoceptors in comparison with our previously studied Ph derivatives All compounds were tested for their α₂-adrenoceptor affinity and unsubstituted guanidinothiophenes displayed the strongest affinities in the same range as the Ph analogs. In the case of cycloalkyl systems, thiophenes with 6-membered rings showed the largest affinities, while for the thiazoles the 5-membered analog presented the strongest affinity. From all the compounds tested for noradrenergic activity, only one compound exhibited agonistic activity, while two compounds showed very promising antagonism of α₂-adrenoceptors. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Reference of 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Reference of 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Straightforward conversion of arene carboxylic acids into aryl nitriles by palladium-catalyzed decarboxylative cyanation reaction was written by Ouchaou, Kahina;Georgin, Dominique;Taran, Frederic. And the article was included in Synlett in 2010.Reference of 55406-13-8 This article mentions the following:

A one-pot procedure to convert aromatic carboxylic acids into aromatic nitriles was described. The methodol. is based on a palladium(II)-catalyzed decarboxylative cyanation reaction using cyanohydrins as soluble cyanide sources. The described reaction worked on a panel of substrates and is addnl. of particular interest for the straightforward preparation of ¹³C- or ¹⁴C-labeled compounds In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Reference of 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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.Reference of 55406-13-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A CaO catalyzed facile one-pot synthesis of 2-aminothiophenes using Gewald reaction was written by Durgareddy, G. A. N. K.;Ravikumar, R.;Ravi, S.;Adapa, Srinivas R.. And the article was included in Pharma Chemica in 2013.Formula: C8H8N2S This article mentions the following:

A series of 2-aminothiophene derivatives I [R¹ = H, Me, Ph, etc.; R² = H, Me, COOEt, etc.; X = COOEt, CN] was synthesized via heterogeneous CaO catalyzed Gewald reaction of an active nitrile or Et ester with ketones in presence of elemental sulfur in ethanol. The present protocol offers several advantages such as low cost material CaO as a catalyst with good yields, shorter reaction time, simple exptl. procedures and low catalyst loading. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Formula: C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. 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.Formula: C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis, Characterization, and Reactivity of Arylpalladium Cyanoalkyl Complexes: Selection of Catalysts for the α-Arylation of Nitriles was written by Culkin, Darcy A.;Hartwig, John F.. And the article was included in Journal of the American Chemical Society in 2002.HPLC of Formula: 5351-07-5 This article mentions the following:

A new coupling process, the Pd-catalyzed α-arylation of nitriles, was developed by exploring the structure and reactivity of arylpalladium cyanoalkyl complexes. Complexes L₂Pd(Ar)(RR¹CCN) (L₂ = DPPBz Ar = C₆H₄Bu-t-4 R = R¹ = H (1), Ar = C₆H₄Me-4, R = H R¹ = Pr-i (2), Ph (3), R = R¹ = Me (4); L₂ = DⁱPrPF, Ar = C₆H₄Bu-t-4, R = H R¹ = Ph (5); L₂ = BINAP, Ar = C₆H₄Bu-t-4, R = H R¹ = Pr-i (7), R = R¹ = Me (8)) or (DⁱPrPF)Pd(C₆H₄Bu-t-4)(N:C:C(CH₃)₂) (6) where DPPBz = 1,2-bis(diphenylphosphino)benzene, DⁱPrPF = 1,1′-bis(diisopropylphosphino)ferrocene, BINAP = (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, and {Pd(PPh₂Et)(C₆H₄Me-4)(μ-CMe₂CN)}₂ (9) were prepared The mol. structures of 4, 6, and 9 were determined by single crystal x-ray anal. Coordination to Pd through the α-C was observed for DPPBz-ligated complexes and for complexes of primary and benzylic nitrile anions. However, the anion of isobutyronitrile was coordinated to Pd through the cyano-N when the complex was ligated by DⁱPrPF. The isobutyronitrile anion displaced a phosphine ligand to form a C,N-bridged dimer when generated from PPh₂Et-ligated Pd. These results suggest that the nitrile anion preferentially coordinates to Pd through the C atom in the absence of steric effects. Thermolysis of the arylpalladium cyanoalkyl complexes led to reductive elimination that formed α-aryl nitriles. The high yields and short reaction times observed for BINAP-ligated complexes suggested that BINAP-ligated Pd catalysts might be appropriate for the arylation of nitriles. Initial results on a Pd-catalyzed process for the direct coupling of aryl bromides and primary, benzylic, and secondary nitrile anions to form α-aryl nitriles in good yields are reported. E.g., addition of a toluene solution containing Me₂CHCN and the base NaN(SiMe₃)₂ to a suspension of Pd(OAc)₂, BINAP, and 4-NCC₆H₄Br in toluene gave 4-NCC₆H₄CMe₂CN in 99% yield after being stirred for 1 h at 100°. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5HPLC of Formula: 5351-07-5).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.HPLC of Formula: 5351-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts