Tag: 200-300

Staron, Jakub; Pietrus, Wojciech; Bugno, Ryszard; Kurczab, Rafal; Satala, Grzegorz; Warszycki, Dawid; Lenda, Tomasz; Wantuch, Anna; Hogendorf, Adam S.; Hogendorf, Agata; Duszynska, Beata; Bojarski, Andrzej J. published an article in 2021. The article was titled 《Tuning the activity of known drugs via the introduction of halogen atoms, a case study of SERT ligands – Fluoxetine and fluvoxamine》, and you may find the article in European Journal of Medicinal Chemistry.Electric Literature of C7H3BrFN The information in the text is summarized as follows:

To elucidate the role of halogen atoms in the binding of SSRIs to SERT, a series of 22 fluoxetine and fluvoxamine analogs substituted with fluorine, chlorine, bromine, and iodine atoms, differently arranged on the Ph ring was designed. The obtained biol. activity data, supported by a thorough in silico binding mode anal., allowed the identification of two partners for halogen bond interactions: the backbone carbonyl oxygen atoms of E493 and T497. Addnl., compounds with heavier halogen atoms were found to bind with the SERT via a distinctly different binding mode, a result not presented elsewhere. The subsequent anal. of the prepared XSAR sets showed that E493 and T497 participated in the largest number of formed halogen bonds. The XSAR library anal. led to the synthesis of two of the most active compounds (3,4-diCl-fluoxetine, SERT Ki = 5 nM and 3,4-diCl-fluvoxamine, SERT Ki = 9 nM, fluoxetine SERT Ki = 31 nM, fluvoxamine SERT Ki = 458 nM). An example of the successful use of a rational methodol. was presented to analyze binding and design more active compounds by halogen atom introduction. ‘XSAR library anal.’, a new tool in medicinal chem., was instrumental in identifying optimal halogen atom substitution. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Electric Literature of C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Electric Literature of C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《ipso-Hydroxylation of Arylboronic Acids and Boronate Esters by Using Sodium Chlorite as an Oxidant in Water》 were Gogoi, Pranjal; Bezboruah, Pranjal; Gogoi, Junali; Boruah, Romesh C.. And the article was published in European Journal of Organic Chemistry in 2013. Application In Synthesis of 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile The author mentioned the following in the article:

A facile and efficient procedure for the ipso-hydroxylation of arylboronic acids to phenols in water was developed. A series of electron-rich and electron-deficient arylboronic acids were smoothly ipso-hydroxylated with this protocol to afford products in excellent yields. Moreover, the protocol is amenable to boronate esters. In most cases, the phenolic products were obtained in pure form without any chromatog. purification In the experiment, the researchers used many compounds, for example, 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7Application In Synthesis of 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile)

2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7) 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. Organic compounds containing multiple nitrile groups are known as cyanocarbons.Application In Synthesis of 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pan, Zhangjin; Li, Wenbo; Zhu, Shuai; Liu, Feng; Wu, Hai-Hong; Zhang, Junliang published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Palladium/TY-Phos-Catalyzed Asymmetric Intermolecular α-Arylation of Aldehydes with Aryl Bromides》.Computed Properties of C7H3BrFN The article contains the following contents:

Herein, an efficient Pd-catalyzed asym. intermol. α-arylation reaction of α-alkyl-α-aryl disubstituted aldehydes with aryl bromides, which provided a rapid access to chiral aldehydes bearing an α-all-carbon quaternary stereocenter in moderate to good yields with good er in most cases was reported. In addition, a pair of enantiomers could be easily prepared with the use of the same ligand by exchanging the aryl groups of aldehyde and aryl bromide.4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Computed Properties of C7H3BrFN) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Computed Properties of C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Welin, Eric R.; Le, Chip; Arias-Rotondo, Daniela M.; McCusker, James K.; MacMillan, David W. C. published 《Photosensitized, energy transfer-mediated organometallic catalysis through electronically excited nickel(II)》.Science (Washington, DC, United States) published the findings.Category: nitriles-buliding-blocks The information in the text is summarized as follows:

Transition metal catalysis has traditionally relied on organometallic complexes that can cycle through a series of ground-state oxidation levels to achieve a series of discrete yet fundamental fragment-coupling steps. The viability of excited-state organometallic catalysis via direct photoexcitation has been demonstrated. Although the utility of triplet sensitization by energy transfer has long been known as a powerful activation mode in organic photochem., it is surprising to recognize that photosensitization mechanisms to access excited-state organometallic catalysts have lagged far behind. Here, we demonstrate excited-state organometallic catalysis via such an activation pathway: Energy transfer from an iridium sensitizer produces an excited-state nickel complex that couples aryl halides with carboxylic acids. Detailed mechanistic studies confirm the role of photosensitization via energy transfer. In the part of experimental materials, we found many familiar compounds, such as 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Category: nitriles-buliding-blocks)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liras, Spiros; Lynch, Christopher L.; Fryer, Andrew M.; Vu, Binh T.; Martin, Stephen F. published an article in Journal of the American Chemical Society. The title of the article was 《Applications of Vinylogous Mannich Reactions. Total Syntheses of the Ergot Alkaloids Rugulovasines A and B and Setoclavine》.Application of 89245-35-2 The author mentioned the following in the article:

Concise syntheses of the Ergot alkaloids rugulovasine A [I; R1 = H, R2 = β-H, R3 = Me, (II)], rugulovasine B I [R1 = H, R2 = α-H, R3 = Me (III)], and setoclavine (IV) have been completed by strategies that feature inter- and intramol. vinylogous Mannich reactions as the key steps. Thus, the first synthesis of II,III commenced with the conversion of the known 4-bromoindole-3-acetonitrile into V via the addition of the 2-(tert-butyldimethylsilyloxy)-3-methylfuran to the iminium ion [VI; CH=N+(Me)Bn], which was generated in situ from the aldehyde VI (R = CHO). Cyclization of V by a novel SRN1 reaction followed by removal of the N-benzyl group furnished a mixture (1:2) of II and III. In an alternative approach to these alkaloids, the biaryl [VII; R = Boc] was reduced with DIBAL-H to give an intermediate imine that underwent spontaneous cyclization via an intramol. vinylogous Mannich addition to provide I [R1 = Boc, R2 = R3 = H]. N-Methylation of the derived benzyl carbamates I [R1 = Boc, R2 = H, R3 = Cbz] followed by global deprotection gave a mixture (2:1) of II and III. IV was then prepared from the biaryl VII (R = Ts) using a closely related intramol. vinylogous Mannich reaction to furnish the spirocyclic lactones I [R1 = Ts, R2 = R3 = H (VIII)]. VIII were subsequently transformed by hydride reduction and reductive methylation into the ergoline derivatives [IX; R = α-OH, β-OH] which were in turn converted into IV by deprotection and solvolytic 1,3-rearrangement of the allylic hydroxyl group. In the experimental materials used by the author, we found 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Application of 89245-35-2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Application of 89245-35-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

COA of Formula: C7H3BrFNIn 2019 ,《Discovery of novel pan-genotypic HCV NS5A inhibitors containing a novel tetracyclic core》 was published in Bioorganic & Medicinal Chemistry Letters. The article was written by Yu, Wensheng; Hu, Bin; Zhong, Bin; Hao, Jinglai; Lei, Zhixin; Agrawal, Sony; Rokosz, Laura; Liu, Rong; Chen, Shiying; Asante-Appiah, Ernest; Kozlowski, Joseph A.. The article contains the following contents:

A series of novel tetracyclic core-containing HCV NS5A inhibitors has been discovered. Incorporation of tetrahydropyran-substituted amino acid moiety improved their potency and yielded HCV NS5A inhibitors with a min. potency shift from the GT1a strain compared to other genotypes and mutants. Compounds 53 and 54 showed the best potency profile and had reasonable half-times in rat PK studies. However, further optimization of their oral bioavailability is still needed in order to advance them for further development. [BMCL Abstract] 2000 Elsevier Science Ltd. All rights reserved. In addition to this study using 4-Bromo-2-fluorobenzonitrile, there are many other studies that have used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3COA of Formula: C7H3BrFN) was used in this study.

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

Staron, Jakub; Pietrus, Wojciech; Bugno, Ryszard; Kurczab, Rafal; Satala, Grzegorz; Warszycki, Dawid; Lenda, Tomasz; Wantuch, Anna; Hogendorf, Adam S.; Hogendorf, Agata; Duszynska, Beata; Bojarski, Andrzej J. published an article in 2021. The article was titled 《Tuning the activity of known drugs via the introduction of halogen atoms, a case study of SERT ligands – Fluoxetine and fluvoxamine》, and you may find the article in European Journal of Medicinal Chemistry.Electric Literature of C7H3BrFN The information in the text is summarized as follows:

To elucidate the role of halogen atoms in the binding of SSRIs to SERT, a series of 22 fluoxetine and fluvoxamine analogs substituted with fluorine, chlorine, bromine, and iodine atoms, differently arranged on the Ph ring was designed. The obtained biol. activity data, supported by a thorough in silico binding mode anal., allowed the identification of two partners for halogen bond interactions: the backbone carbonyl oxygen atoms of E493 and T497. Addnl., compounds with heavier halogen atoms were found to bind with the SERT via a distinctly different binding mode, a result not presented elsewhere. The subsequent anal. of the prepared XSAR sets showed that E493 and T497 participated in the largest number of formed halogen bonds. The XSAR library anal. led to the synthesis of two of the most active compounds (3,4-diCl-fluoxetine, SERT Ki = 5 nM and 3,4-diCl-fluvoxamine, SERT Ki = 9 nM, fluoxetine SERT Ki = 31 nM, fluvoxamine SERT Ki = 458 nM). An example of the successful use of a rational methodol. was presented to analyze binding and design more active compounds by halogen atom introduction. ‘XSAR library anal.’, a new tool in medicinal chem., was instrumental in identifying optimal halogen atom substitution. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Electric Literature of C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Electric Literature of C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wang, Xing-Rong; Wang, Shuai; Li, Wen-Bo; Xu, Kai-Yan; Qiao, Xue-Peng; Jing, Xue-Li; Wang, Zi-Xiao; Yang, Chang-jiang; Chen, Shi-Wu published an article in 2021. The article was titled 《Design, synthesis and biological evaluation of novel 2-(4-(1H-indazol-6-yl)-1H-pyrazol-1-yl)acetamide derivatives as potent VEGFR-2 inhibitors》, and you may find the article in European Journal of Medicinal Chemistry.Product Details of 105942-08-3 The information in the text is summarized as follows:

Vascular endothelial growth factor-2 (VEGFR-2) plays a pivotal role in tumor angiogenesis. Herein, a library of novel 2-(4-(1H-indazol-6-yl)-1H-pyrazol-1-yl)acetamide derivatives were designed and synthesized as VEGFR-2 inhibitors based on scaffold hopping strategy. These compounds exhibited excellent inhibitory activity in both VEGFR-2 and tumor cell proliferation. Especially, compound I possessed potent VEGFR-2 inhibition with IC50 = 1.6 nM and anti-proliferation against HGC-27 tumor cells with IC50 = 0.36 +/- 0.11μM, as well as less toxicity against normal GES-1 cells with IC50 = 187.46 +/- 10.13μM. Moreover, I obviously inhibited colony formation, migration and invasion of HGC-27 cells by adjusting the expression of MMP-9 and E-cadherin, and induced HGC-27 cells apoptosis by increasing ROS production and regulates the expression of apoptotic proteins. Furthermore, I blocked the PI3K-Akt-mTOR signaling pathway in HGC-27 cells. In addition, anti-angiogenesis of I was proved by inhibition tube formation and the expression of p-VEGFR-2 in HUVEC cells. All the results demonstrated that I could be developed as a promising anticancer agent for gastric cancer therapy. After reading the article, we found that the author used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Product Details of 105942-08-3)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2018,Scheidt, Felix; Schaefer, Michael; Sarie, Jerome C.; Daniliuc, Constantin G.; Molloy, John J.; Gilmour, Ryan published 《Enantioselective, Catalytic Vicinal Difluorination of Alkenes》.Angewandte Chemie, International Edition published the findings.SDS of cas: 105942-08-3 The information in the text is summarized as follows:

An efficient method was developed for the synthesis of 1,2-difluoroethyl arenes ArCH(F)CH2F [Ar = 3-CNC6H4, 4-O2NC6H4, 2-SO2MeC6H4, etc.] via enantioselective II/IIII catalytic vicinal difluorination of terminal alkenes using novel C2-sym. resorcinol derivative Catalyst turnover via in situ generation of an ArIIIIF2 species was enabled by Selectfluor oxidation and addition of an inexpensive HF-amine complex. The HF:amine ratio employed in this process provided a handle for regioselective orthogonality as a function of Bronsted acidity. Selectivity reversal from the 1,1-difluorination pathway (geminal) to the desired 1,2-difluorination (vicinal) was disclosed (>20:1 in both directions). An achiral variant of the reaction was also presented using p-iodotoluene (up to >95 % yield). In the part of experimental materials, we found many familiar compounds, such as 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3SDS of cas: 105942-08-3)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.SDS of cas: 105942-08-3 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Ketels, Marthe; Ganiek, Maximilian A.; Weidmann, Niels; Knochel, Paul published 《Synthesis of Polyfunctional Diorganomagnesium and Diorganozinc Reagents through In Situ Trapping Halogen-Lithium Exchange of Highly Functionalized (Hetero)aryl Halides in Continuous Flow》.Angewandte Chemie, International Edition published the findings.Product Details of 105942-08-3 The information in the text is summarized as follows:

Using com. available flow reactors, di(hetero)arylmagnesium and di(hetero)arylzinc reagents containing normally incompatible functional groups such as azides, nitro groups, isothiocyanates, esters, and ketones were generated in situ by lithium-metal exchange reactions of aryl bromides or iodides such as 1-azido-4-iodobenzene with BuLi or PhLi and transmetalation with either MgCl2·LiCl or ZnCl2. Reaction of the di(hetero)arylmagnesium and di(hetero)arylzinc reagents with electrophiles such as allyl bromide, cyclopropanecarbonyl chloride, and cyclopropyl 4-fluorophenyl ketone mediated by CuCN·2 LiCl or palladium-catalyzed coupling reactions yielded (hetero)arene-containing products such as 4-N3C6H4CH2CH:CH2 in 62-85% yields. The preparation of 4-(4-bromobenzoyl)-2-fluorobenzonitrile was performed by this method on 10 mmol scale without further optimization. The experimental process involved the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Product Details of 105942-08-3)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Product Details of 105942-08-3 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts