Category: nitriles-buliding-blocks

Application of 105942-08-3In 2018 ,《Design, synthesis and evaluate of novel dual FGFR1 and HDAC inhibitors bearing an indazole scaffold》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Liu, Jian; Qian, Chengbo; Zhu, Yehua; Cai, Jianguo; He, Yufang; Li, Jie; Wang, Tianlin; Zhu, Haohao; Li, Zhi; Li, Wei; Hu, Lihong. The article conveys some information:

Both histone deacetylase (HDAC) and fibroblast growth factor receptor (FGFR) are important targets for cancer therapy. Although combining dual HDAC pharmacophore with tyrosine kinase inhibitors (TKIs) had achieved a successful progress, dual HDAC/FGFR1 inhibitors haven’t been reported yet. Herein, we designed a series of hybrids bearing 1H-indazol-3-amine and benzohydroxamic acids scaffold with scaffold hopping and mol. hybridization strategies. Among them, compound 7j showed the most potent inhibitory activity against HDAC6 with IC50 of 34 nM and exhibited the great inhibitory activities against a human breast cancer cell line MCF-7 with IC50 of 9 μM in vitro. Meanwhile, the compound also exhibited moderate FGFR1 inhibitory activities. This study provides new tool compounds for further exploration of dual HDAC/FGFR1 inhibition. In addition to this study using 4-Bromo-2-fluorobenzonitrile, there are many other studies that have used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Application of 105942-08-3) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Application of 105942-08-3 It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Nguyen, Thuy; Gamage, Thomas F.; Finlay, David B.; Decker, Ann M.; Langston, Tiffany L.; Barrus, Daniel; Glass, Michelle; Li, Jun-Xu; Kenakin, Terry P.; Zhang, Yanan published an article in Journal of Medicinal Chemistry. The title of the article was 《Development of 3-(4-Chlorophenyl)-1-(phenethyl)urea Analogues as Allosteric Modulators of the Cannabinoid Type-1 Receptor: RTICBM-189 is Brain Penetrant and Attenuates Reinstatement of Cocaine-Seeking Behavior》.Formula: C8H6BrN The author mentioned the following in the article:

We have shown that CB1 receptor neg. allosteric modulators (NAMs) attenuated the reinstatement of cocaine-seeking behaviors in rats. In an effort to further define the structure-activity relationships and assess the druglike properties of the 3-(4-chlorophenyl)-1-(phenethyl)urea-based CB1 NAMs that we recently reported, we introduced substituents of different electronic properties and sizes to the phenethyl group and evaluated their potency in CB1 calcium mobilization, cAMP, and GTPγS assays. We found that 3-position substitutions such as Cl, F, and Me afforded enhanced CB1 potency, whereas 4-position analogs were generally less potent. The 3-chloro analog (31, RTICBM-189)(I) showed no activity at >50 protein targets and excellent brain permeation but relatively low metabolic stability in rat liver microsomes. Pharmacokinetic studies in rats confirmed the excellent brain exposure of 31 with a brain/plasma ratio Kp of 2.0. Importantly, i.p. administration of 31 significantly and selectively attenuated the reinstatement of the cocaine-seeking behavior in rats without affecting locomotion. In addition to this study using 2-(3-Bromophenyl)acetonitrile, there are many other studies that have used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Formula: C8H6BrN) was used in this study.

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Formula: C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Joy, F.; Peter, F.; Gokul, P. C.; Nizam, A.; Chinnam, S. published an article in 2022. The article was titled 《UV-Promoted Metal- and Photocatalyst-Free Direct Conversion of Aromatic Aldehydes to Nitriles》, and you may find the article in Russian Journal of Organic Chemistry.Quality Control of 4-Fluorobenzonitrile The information in the text is summarized as follows:

An efficient, simple and catalyst-free UV-induced functional group transformation of aromatic aldehydes to nitriles was reported. The developed strategy delivered various functionalized aromatic nitriles with high yields and purity. The UV irradiation activated the carbonyl group of aldehydes and lead to the formation of aldoxime intermediate, further resulting in the generation of nitriles. The striking highlights of the reported methodol. were simple reaction conditions, good yields, UV-promoted transformation and catalyst-free synthesis. Due to the above-mentioned advantages, the methodol. provided a hand towards environmentally friendly chem. synthesis. In the experiment, the researchers used many compounds, for example, 4-Fluorobenzonitrile(cas: 1194-02-1Quality Control of 4-Fluorobenzonitrile)

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.Quality Control of 4-Fluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Lu, Wen-Xiu; Xing, Jian; Sun, Yijia; Huang, Qinge; Deng, Zhenwei; Mao, Jian-Gang published their research in Organic & Biomolecular Chemistry in 2021. The article was titled 《Palladium-catalyzed and alcohol-enabled transformation to synthesize benzocyclic ketones》.Formula: C7H4BrN The article contains the following contents:

A highly effective palladium-catalyzed and alc.-promoted transformation of nitriles to synthesize benzocyclic ketones was described. It provided a straightforward access to potentially valuable indanone compounds in high yields in the presence of alc. It avoided the usage of carbon monoxide or an addnl. hydrolysis procedure. In the part of experimental materials, we found many familiar compounds, such as 2-Bromobenzonitrile(cas: 2042-37-7Formula: C7H4BrN)

2-Bromobenzonitrile(cas: 2042-37-7) is a precursor to the quinazolinones, a class of drugs used to treat autoimmune diseases and coronary heart disease. This substrate molecule undergoes a palladium-catalyzed coupling reaction to form an aromatic ring. The light emission from this reaction can be seen in the reaction solution.Formula: C7H4BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wei, Yueting; Liu, Ping; Liu, Yali; He, Jing; Li, Xuezhen; Li, Shiwu; Zhao, Jixing published their research in Organic & Biomolecular Chemistry in 2021. The article was titled 《NIS-promoted three-component reaction of 3-oxo-3-arylpropanenitriles with arylsulfonyl hydrazides》.Related Products of 614-16-4 The article contains the following contents:

A new three-component reaction of 3-oxo-3-arylpropanenitriles with arylsulfonyl hydrazides was established and an expanded inventory of 3-aryl-4-(arylthio)-1H-pyrazol-5-amines were synthesized by sequential cyclization and sulfenylation reactions under the action of NIS. In addition to the attractive features of multicomponent reactions, the protocol presented broad substrate scope, good functional group tolerance and mild reaction conditions. The utility of this procedure was further established by gram-scale synthesis as well as the diversified transformations of the products to useful compounds After reading the article, we found that the author used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Related Products of 614-16-4)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Related Products of 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Regioselective functionalization of aryl azoles as powerful tool for the synthesis of pharmaceutically relevant targets》 was written by Lutter, Ferdinand H.; Grokenberger, Lucie; Perego, Luca Alessandro; Broggini, Diego; Lemaire, Sebastien; Wagschal, Simon; Knochel, Paul. COA of Formula: C7H3BrFN And the article was included in Nature Communications in 2020. The article conveys some information:

The metalation of 1-aryl-1H-1,2,3-triazoles and other related heterocycles with sterically hindered metal-amide bases were investigated. A room temperature and highly regioselective ortho-magnesiation of several aryl azoles using a tailored magnesium amide, TMPMgBu (TMP = 2,2,6,6-tetramethylpiperidyl) in hydrocarbon solvents followed by an efficient Pd-catalyzed arylation was reported. This scalable and selective reaction allows variation of the initial substitution pattern of the aryl ring, the nature of the azole moiety, as well as the nature of the electrophile. This versatile method can be applied to the synthesis of bioactive azole derivatives and complements existing metal-mediated ortho-functionalizations. In the experiment, the researchers used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3COA of Formula: C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.COA of Formula: C7H3BrFN It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2014,Yan, Zi-Hong; Huang, Xia-Yun; Wu, Hai-Qiu; Chen, Wen-Xue; He, Qiu-Qin; Chen, Fen-Er; De Clercq, Erik; Pannecouque, Christophe published 《Structural modifications of CH(OH)-DAPYs as new HIV-1 non-nucleoside reverse transcriptase inhibitors》.Bioorganic & Medicinal Chemistry published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

A series of CR2(OH)-diarylpyrimidine derivatives (CR2(OH)-DAPYs) featuring a hydrophobic group at CH(OH) linker between wing I and the central pyrimidine were synthesized and evaluated for their anti-HIV activity in MT-4 cell cultures. All the target compounds except for compound 3k displayed inhibitory activity against HIV-1 wild-type with EC50 values ranging from 7.21 ± 1.99 to 0.067 ± 0.006μM. Among them, compound 3d showed the most potent anti-HIV-1 activity (EC50 = 0.067 ± 0.006μM, SI > 592), which was approx. 2-fold more potent than the reference drugs nevirapine (NVP) and delavirdine (DLV) in the same assay. In addition, the binding modes with HIV-1 RT and the preliminary SAR studies of these new derivatives were also investigated.2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5) was used in this study.

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Product Details of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2014,Yan, Zi-Hong; Wu, Hai-Qiu; Chen, Wen-Xue; Wu, Yan; Piao, Hu-Ri; He, Qiu-Qin; Chen, Fen-Er; De Clercq, Erik; Pannecouque, Christophe published 《Synthesis and biological evaluation of CHX-DAPYs as HIV-1 non-nucleoside reverse transcriptase inhibitors》.Bioorganic & Medicinal Chemistry published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

A series of new diarylpyrimidines (DAPYs) characterized by a halogen atom on the methylene linker between wing I and the central pyrimidine ring was synthesized and evaluated for their anti-HIV activity in MT-4 cell cultures. The two most promising compounds 7f and 7g showed excellent activity against wild-type HIV-1 with low nanomolar EC50 values of 0.005 and 0.009μM, resp., which were comparable to or more potent than all the reference drugs zidovudine (AZT), lamivudine (3TC), nevirapine (NEV), efavirenz (EFV), delavirdine (DLV) and etravirine (ETV). In particular, 7g also displayed strong activity against the double mutant strain 103N + 181C with an EC50 value of 8.2μM. The preliminary structure-activity relationship (SAR) and mol. docking anal. of this new series of CHX-DAPYs were also investigated. In the part of experimental materials, we found many familiar compounds, such as 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5)

According to other reports, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) is used in the preparation of diarylpyrimidines (DAPYs) as HIV-1 non-nucleoside reverse transcriptase inhibitors.Product Details of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2012,Pesnot, Thomas; Gershater, Markus C.; Ward, John M.; Hailes, Helen C. published 《The Catalytic Potential of Coptis japonica NCS2 Revealed – Development and Utilisation of a Fluorescamine-Based Assay》.Advanced Synthesis & Catalysis published the findings.Synthetic Route of C8H6BrN The information in the text is summarized as follows:

The versatility and potential of a norcoclaurine synthase (NCS) from Coptis japonica NCS2 has been investigated, together with the development and application of a novel fluorescence-based high-throughput assay using nearly forty amines/aldehydes. The stereocontrol exerted by CjNCS2 on selected non-natural substrates has been determined, where the tetrahydroisoquinolines (THIAs) were formed as the (1S)-isomer in >95% ee, as observed with the natural product norcoclaurine. Docking calculations involving THIA mechanism intermediates, utilizing the reported Thalictrum flavum NCS X-ray crystallog. structure, were carried out and combined with the CjNCS2 screening results to further understand the mode of action of NCS. These findings suggested that in addition to the key active-site residues K122 and E110, D141 is also mechanistically essential for the enzymic transformation. The exceptional tolerance of NCS towards aldehyde substrates is furthermore supported by our proposed mechanism in which the aldehydes protrude out of the enzymic pocket. After reading the article, we found that the author used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Synthetic Route of C8H6BrN)

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Synthetic Route of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Studies on antianaphylactic agents. 7. Synthesis of antiallergic 5-oxo-5H-[1]benzopyrano[2,3-b]pyridines》 were Nohara, Akira; Ishiguro, Toshihiro; Ukawa, Kiyoshi; Sugihara, Hirosada; Maki, Yoshitaka; Sanno, Yasushi. And the article was published in Journal of Medicinal Chemistry in 1985. Name: 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile The author mentioned the following in the article:

5-Oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acids I and their tetrazole analogs II (R = H, Me, OH, amino; R1 = H, Me; R2 = H, Me, Et, Me2CH, Bu, Me3C, OMe; R1R2 = CH:CHCH:CH) were prepared from 4-oxo-4H-1-benzopyran-3-carbonitriles or 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehydes. They exhibited antiallergic activity both orally and i.v. in the passive cutaneous anaphylaxis test in rats. With I, the activity was influenced by the substituents at the 2-position and increased in the order: Me, OMe < NH2 < OH, H < NHOMe. Tetrazole series with II, 2-unsubsituted derivatives showed the highest activity. In addition to this study using 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile, there are many other studies that have used 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3Name: 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile) was used in this study.

6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3) belongs to nitriles. Nitriles are found in many useful compounds. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Name: 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile 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.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts