Tag: 100-200

In 2015,He, Wu; Zhou, Bin; Liu, Weijia; Zhang, Meizi; Shen, Zhenhua; Han, Zhifu; Jiang, Qingwei; Yang, Qinghua; Song, Chuanjun; Wang, Ruiyong; Niu, Tianhui; Han, Shengna; Zhang, Lirong; Wu, Jie; Guo, Feima; Zhao, Renbin; Yu, Wenquan; Chai, Jijie; Chang, Junbiao published 《Identification of A Novel Small-Molecule Binding Site of the Fat Mass and Obesity Associated Protein (FTO)》.Journal of Medicinal Chemistry published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

N-(5-Chloro-2,4-dihydroxyphenyl)-1-phenylcyclobutanecarboxamide I is found to be an inhibitor of the fat mass and obesity associated protein (FTO). The crystal structure of human FTO with I reveals a novel binding site for the FTO inhibitor and defines the mol. basis for recognition by FTO of the inhibitor. The identification of the new binding site offers new opportunities for further development of selective and potent inhibitors of FTO, which is expected to provide information concerning novel therapeutic targets for treatment of obesity or obesity-associated diseases. The results came from multiple reactions, including the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5)

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 2005,Robertson, Daniel; Cannon, John F.; Gerasimchuk, Nikolay published 《Double-Stranded Metal-Organic Networks for One-Dimensional Mixed Valence Coordination Polymers》.Inorganic Chemistry published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

The design of new types of metal-organic networks and the search for unusual crystal architecture represents an important task for modern inorganic and materials chem. research. A group of new monosubstituted phenylcyanoximes, containing F, Cl, and Br atoms at the 2, 3, or 4 positions, were synthesized using the high yield nitrosation reaction with CH3-ONO and were spectroscopically (1H NMR, 13C NMR, UV-visible, IR, mass spectrometry) and structurally characterized. Results of x-ray anal. revealed nonplanar trans-anti geometry for 2-chlorophenyl(oximino)acetonitrile, H(2Cl-PhCO); a nonplanar anti configuration for 4-chlorophenyl(oximino)acetonitrile, H(4Cl-PhCO); and planar cis-syn geometry for 3-fluorophenyl(oximino)acetonitrile, H(3F-PhCO). All arylcyanoximes undergo deprotonation in solutions with the formation of colored anions exhibiting pronounced neg. solvatochromism in polar protic and aprotic solvents. Nine Tl(I) cyanoximates were obtained using the reaction between hot (∼95°) aqueous solutions of Tl2CO3 and solid powdery monohalogenated arylcyanoximes HL. Crystal structures of two Tl(I) cyanoximates [Tl(2Cl-PhCO) and Tl(4Br-PhCO)] contained centrosym. dimeric units (TlL)2 that are connected to a coordination polymer by an O atom of the oxime group of the neighboring mol. Cyanoxime anions act as bridging ligands in both structures where the polymeric motif consists of double-stranded Tl-O chains interconnected with the formation of zigzagging Tl2O2 planar rhombes. Tl atoms form infinite linear arrays with close intermetallic separations The nearest Tl(I)···Tl(I) distances are 3.838 and 4.058 Å in the Tl(2Cl-PhCO) and Tl(4Br-PhCO) structures, resp., close to that in metallic Tl (3.456 Å). Monosubstituted Ph groups are well aligned in π-stacking columns that are perpendicular to the array of Tl(I) atoms and stabilize formed structures. Coordination polyhedrons of Tl(I) in these complexes represent distorted trigonal pyramids with stereoactive lone pair. After reading the article, we found that the author used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5)

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

SDS of cas: 614-16-4In 2019 ,《Chemo- and Diastereoselective Synthesis of Pyrazolo-tetrahydropyridines via Multicomponent Sequential Aza-Diels-Alder Reactions in Water》 appeared in ChemistrySelect. The author of the article were Nazeri, Mohammad Taghi; Javanbakht, Siamak; Shaabani, Ahmad; Khavasi, Hamid Reza. The article conveys some information:

A novel and an efficient strategy for the synthesis of chemo- and diastereoselective synthesis of pyrazolo-tetrahydropyridines I [X = O, NMe; Y = C, SO; R1 = Me, Ph; R2 = H, Br, OMe, naphthyl; Ar = Ph, 4-ClC6H4] via a one-pot multi-component intramol. aza-Diels-Alder reactions (ADARs) from benzoylacetonitrile derivatives, phenylhydrazine, salicylaldehyde derivatives, and styrenesulfonyl or cinnamoyl chloride in H2O as a green solvent was reported. This synthesis procedure was also designed to follow the group-assisted purification (GAP) chem., which could avoid traditional purification such as recrystallization and chromatog. methods.3-Oxo-3-phenylpropanenitrile(cas: 614-16-4SDS of cas: 614-16-4) was used in this study.

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used in the synthesis of substituted naphtho[1,8-bc]pyrans. It was also used as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.SDS of cas: 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Shi, Jianyi; Zeng, Zheng; Xu, Shengting; Cai, Zechun; Luo, Yuehua; Fan, Yongbo; Zhu, Zhongzhi; Wen, Tingting; Chen, Xiuwen published an article in Chinese Chemical Letters. The title of the article was 《Cross-coupling of 2-methylquinolines and in-situ activated isoquinolines: Construction of 1,2-disubstituted isoquinolinones》.Application In Synthesis of 4-Cyanobenzyl bromide The author mentioned the following in the article:

In this study, a method was developed to form C(sp3)-C(sp2) bonds via copper catalyst-promoted cross coupling of 2-methylquinolines I (R1 = H, 6-Me, 7-Cl, etc.) and in-situ-activated 3-haloisoquinolines II (R2 = H, 5-Br, 4-Br; X = Br, Cl) under mild conditions. The multi-component tandem reaction was used to construct new C-N, C=O and C-C bonds in one pot via sequential functionalization of the N1, C3 and C1 positions of 3-haloisoquinolines. This method can be used to efficiently access 1,2-disubstituted isoquinolinones III (R4 = H, 6-Br, 7-Br) by the three-component reaction of 3-halogen isoquinolines, alkyl halides R3CH2Y (R3 = Ph, 2,4-difluorophenyl, 2-naphthyl, etc.; Y = Br, Cl), and 2-methylquinolines. In the part of experimental materials, we found many familiar compounds, such as 4-Cyanobenzyl bromide(cas: 17201-43-3Application In Synthesis of 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) is an important intermediate for pharmaceutical production. It can be used for the synthesis of a series of piperidine-linked aromatic diimidazolines, which have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii (PCP) drug, Pentamidine.Application In Synthesis of 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Zhang, Cheng; Chen, Qian; Wang, Lei; Sun, Qiaoying; Yang, Yangyang; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K. published an article in Science China: Chemistry. The title of the article was 《Practical and modular construction of benzo[c]phenanthridine compounds》.COA of Formula: C7H4BrN The author mentioned the following in the article:

Herein, a general and modular strategy for the rapid assembly of benzo[c]phenanthridine (BCP) derivatives I [R = tBu, adamantan-1-yl; R1 = H, 9-Me, 8-OMe, etc.; R2 = H, 3-F, 2-OMe, etc.], II [R3 = tBu, Ph, 3-furyl, etc.] using homogeneous gold catalysis was described. Notably, in contrast to traditional methods based on the specially preformed substrates that had an inherent preference for the formation of this class of compounds with limited flexibility, this protocol was achieved via a selectively intramol. cascade of a diazo-tethered alkyne and subsequently an intermol. cyclization with a nitrile to facilitate the successive C-N and C-C bonds formation. This methodol. used readily available nitriles as the nitrogen source to deliver the products I and II in good yield with excellent functional group compatibility. A preliminary anti-tumor activity study of these generated products exhibitd high anticancer potency against five tumor cell lines, including HeLa, Mel624, SW-480, 8505C and LAN-1. Besides, a catalyst-controlled intermol. cycloaddition/intramol. insertion of the substrate with a fulvene to provide fused polycarbocycles containing a seven-membered ring III [R4 = Ph, 3-thienyl, 2-naphthyl, etc.; R5 = H, 11-OMe] was reported.2-Bromobenzonitrile(cas: 2042-37-7COA of Formula: C7H4BrN) was used in this study.

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.COA of Formula: C7H4BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ibrahim, Seham A.; Fayed, Eman A.; Rizk, Hala F.; Desouky, Said E.; Ragab, Ahmed published an article in 2021. The article was titled 《Hydrazonoyl bromide precursors as DHFR inhibitors for the synthesis of bis-thiazolyl pyrazole derivatives; antimicrobial activities, antibiofilm, and drug combination studies against MRSA》, and you may find the article in Bioorganic Chemistry.Formula: C9H7NO The information in the text is summarized as follows:

Microbial resistance is a big concern worldwide, making the development of new antimicrobial drugs difficult. The thiazole and pyrazole rings are important heterocyclic compounds utilized to produce a variety of antimicrobial medications. As a result, a series of new bis-thiazolyl-pyrazole derivatives 3, 4a-c, 5a, b, and 6a-c was synthesized by reacting bis hydrazonoyl bromide with several active methylene reagents in a one-pot reaction. The assigned structure was characterized entirely based on elemental and spectral analyses. The antimicrobial activity represented by MIC was performed using a resazurin-based turbidimetric (TB) assay. The results exhibited good antimicrobial activity against gram-pos. strains, especially S. aureus (ATCC6538) while showing poor to moderate activity against gram-neg. and fungal strains. Furthermore, the most active derivatives 3, 4a, 4c, and 5b were evaluated for MIC, MBC, antibiofilm, hemolytic assay, and drug combination testing against two S. aureus (ATCC6538) and MRSA (ACL18) strains. Addnl., bis-thiazolyl pyrazole 3, 4c, and 5b exhibited more potent inhibitory activity for DHFR with IC50 values (6.34 ± 0.26, 7.49 ± 0.28, and 3.81 ± 0.16 μM), resp., compared with Trimethoprim (8.34 ± 0.11 μM). The bis-1-(substituted-thiazol-2-yl)-1H-pyrazole-4-carbonitrile derivative 5b was the most active member with MIC values ranging from (0.12-0.25 μM) compared to Vancomycin (1-2 μM), and MBC values ranging from (0.5-1 μM) for S. aureus (ATCC6538) and MRSA (ACL18). Surprisingly, compound 5b displayed bactericidal behavior, synergistic effect with three com. antibiotics, and inhibited DHFR with 2.1 folds higher than Trimethoprim. Finally, good findings were obtained from in silico investigations incorporating toxicity prediction and mol. docking simulation. In the experimental materials used by the author, we found 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Formula: C9H7NO)

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.Formula: C9H7NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hussein, Ahmad Q.; Sammor, Mervat S. published their research in Heterocyclic Letters in 2021. The article was titled 《New easy one-pot synthetic routes of 2-arylbenzimidazoles》.Synthetic Route of C9H7NO The article contains the following contents:

One-pot condensation of 1,2-phenylenediamine with phenacyl cyanides affords high yields of the corresponding 2-arylbenzimidazoles. The same products are also obtained through similar condensation of phenylenediamine either with phenacyl thiocyanates or with benzylidenemalononitriles. In the experimental materials used by the author, we found 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Synthetic Route of C9H7NO)

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.Synthetic Route of C9H7NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zeng, Qing-Xuan; Wang, Kun; Zhang, Xin; Shi, Yu-Long; Dou, Yue-Ying; Guo, Zhi-Hao; Zhang, Xin-Tong; Zhang, Na; Deng, Hong-Bin; Li, Ying-Hong; Song, Dan-Qing published their research in Bioorganic Chemistry in 2021. The article was titled 《Structure-activity relationship and biological evaluation of 12 N-substituted aloperine derivatives as PD-L1 down-regulatory agents through proteasome pathway》.Reference of 4-Cyanobenzyl bromide The article contains the following contents:

Twenty-nine 12 N-substituted aloperine derivatives were synthesized and screened for suppression on PD-L1 expression in H460 cells, as a continuation of our work. Systematic structural modifications led to the identification of compound I as the most active PD-L1 modulator. Compound I could significantly down-regulate both constitutive and inductive PD-L1 expression in NSCLC cells, and successively enhance the cytotoxicity of co-cultured T cells against tumor cells at the concentration of 20μM. Also, it exhibited a moderate in vivo anticancer efficacy against Lewis tumor xenograft with a stable PK and safety profile. The mechanism study indicated that I mediated the degradation of PD-L1 through a proteasome pathway, rather than a lysosome route. These results provided the powerful information for cancer immunotherapy of aloperine derivatives with unique endocyclic skeleton by targeting PD-L1 to activate immune cells to kill cancer cells. The experimental part of the paper was very detailed, including the reaction process of 4-Cyanobenzyl bromide(cas: 17201-43-3Reference of 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide.Reference of 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines》 was written by Gao, Peng; Chen, Huai-Juan; Bai, Zi-Jing; Zhao, Mi-Na; Yang, Desuo; Wang, Juan; Wang, Ning; Du, Lele; Guan, Zheng-Hui. Category: nitriles-buliding-blocks And the article was included in Journal of Organic Chemistry in 2020. The article conveys some information:

An iodoxybenzoic acid-mediated selected oxidative cyclization of N-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alc., followed by condensation of aldehyde and α-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally friendly reagents, broad substrate scope, mild reaction conditions, and high efficiency.3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Category: nitriles-buliding-blocks) was used in this study.

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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Synthesis and in-vitro anti-proliferative evaluation of some pyrazolo[1,5-a]pyrimidines as novel larotrectinib analogs》 was published in Bioorganic Chemistry in 2020. These research results belong to Attia, Mohamed H.; Elrazaz, Eman Z.; El-Emam, Soad Z.; Taher, Azza T.; Abdel-Aziz, Hatem A.; Abouzid, Khaled A. M.. Quality Control of 3-Oxo-3-phenylpropanenitrile The article mentions the following:

A series of pyrazolo[1,5-a]pyrimidine-3-carbonitriles I [R = H; Ar = 2-furanyl, Ph, 2-naphthalenyl, etc.] and pyrazolo[1,5-a]pyrimidine-3,6-dicarbonitriles I [R = cyano; Ar = 2-furanyl, Ph, 4-methoxyphenyl] was synthesized by the reaction of 5-amino-3-phenyl-1H-pyrazole-4-carbonitrile with 3-(dimethylamino)-1-arylprop-2-en-1-ones or 2-aryl-3-(dimethylamino)acrylonitriles, resp. In addition, 7-amino-5-oxo-2-phenyl-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile II was prepared from the reaction of dimethylformamide-dimethylacetal with Et cyanoacetate. The anticancer activity of the newly synthesized compounds against Huh-7, HeLa, MCF-7 and MDA-MB231 cell lines showed moderate activity of compound I [R = H, Ar = 4-chlorophenyl] as anti-proliferative agent against Huh-7 cell line with IC50 = 6.3μM when compared with doxorubicin (IC50 = 3.2μM). On the other hand, compound I [R = cyano, Ar = 4-methoxyphenyl] revealed potent anti-proliferative activity against HeLa cell line with IC50 = 7.8μM when compared with doxorubicinι (IC50 = 8.1μM). Also compound I [R = H, Ar = 2-naphthalenyl] exhibited a promising anti-proliferative activity against MCF-7 cell line (IC50 = 3.0μM) whereas IC50 of doxorubicin = 5.9μM, finally compounds I [R = H, Ar = 2-naphthalenyl] and I [R = cyano, Ar = 24-methoxyphenyl] have potent activity as anti-proliferative agents against MDA-MB231 cell line with IC50 = 4.32 and 5.74μM, resp. when compared with doxorubicin (IC50 = 6.0μM). The experimental part of the paper was very detailed, including the reaction process of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Quality Control of 3-Oxo-3-phenylpropanenitrile)

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.Quality Control of 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts