Tag: M.W=150-200

Suzuki, Itaru; Ogura, Kazuki; Shimazu, Jun-ya; Shibata, Ikuya published the artcile< Magnesium Halide-Catalyzed Synthesis of Oxaspiro[2.5]octenes from a Methylenecyclopropane and Acyl Cyanoalkenes>, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is oxaspirooctene preparation diastereoselective chemoselective; methylenecyclopropane acyl cyanoalkene cyclization magnesium halide catalyst.

MgX2-catalyzed annulation of 1,1-di-Et 2-methylidenecyclopropane-1,1-dicarboxylate with acyl cyanoalkenes RC(O)C(CN)=CHAr (R = Me, Ph, 3-chlorophenyl, etc.; Ar = 4-fluorophenyl, 1-naphthyl, 2-furyl, etc.) was accomplished to give oxaspiro[2.5]octenes I (E = C(O)OEt) and II in excellent yields. The reaction proceeded through a rare intramol. oxa-Michael addition of Mg enolate. The oxaspiro ring was transformed into di-Et 2-((5-cyano-4,6-diphenyl-4H-pyran-2-yl)methyl)malonate at a higher temperature in the presence of MgX2.

European Journal of Organic Chemistry published new progress about Chemoselectivity. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Xie, Hao; Li, Guozheng; Zhang, Feng; Xiao, Fuhong; Deng, Guo-Jun published the artcile< Efficient synthesis of 1,2-benzisothiazoles from o-haloarylamidines and elemental sulfur via N-S/C-S bond formation under transition-metal-free conditions>, Formula: C8H6ClN, the main research area is haloaryl phenylamidine preparation sulfur heterocyclization; benzisothiazole preparation.

An efficient method for the synthesis of 1,2-benzisothiazoles from amidines and elemental sulfur via N-S/C-S bond formation under transition-metal-free conditions was described. This reaction was performed smoothly under simple conditions to give the corresponding products in good to high yields with good functional group tolerance.

Green Chemistry published new progress about Amidines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 21423-84-7 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H6ClN, Formula: C8H6ClN.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Paul, Saurav; Roy, Ashalata; Deka, Suman Jyoti; Panda, Subhankar; Trivedi, Vishal; Manna, Debasis published the artcile< Nitrobenzofurazan derivatives of N'-hydroxyamidines as potent inhibitors of indoleamine-2,3-dioxygenase 1>, Application of C8H5F2N, the main research area is nitrobenzofurazan hydroxyamidine preparation inhibitor indoleaminedioxygenase antitumor mol docking; High selectivity; IDO1 inhibition; Low cytotoxicity; Mechanism-based drug design; N′-hydroxyamidines.

Tryptophan metabolism through the kynurenine pathway is considered as a crucial mechanism in immune tolerance. Indoleamine 2,3-dioxygenase 1 (IDO1) plays a key role in tryptophan catabolism in the immune system and it is also considered as an important therapeutic target for the treatment of cancer and other diseases that are linked with kynurenine pathway. Nitrobenzofurazan derivatives of N’-hydroxybenzimidamides and N’-hydroxy-2-phenylacetimidamides were synthesized and their inhibitory activities against human IDO1 enzyme were tested using in-vitro and cellular enzyme activity assay. The optimization leads to the identification of three potent compounds (IC50 = 39-80 nM), which are either competitive or uncompetitive inhibitors of IDO1 enzyme. These compounds also showed IDO1 inhibition potencies in the nanomolar range (IC50 = 50-71 nM) in MDA-MB-231 cells with no/negligible amount of cytotoxicity. The stronger selectivity of the potent compounds for IDO1 enzyme over tryptophan 2,3-dioxygenase (TDO) enzyme (312-1593-fold) also makes them very attractive for further immunotherapeutic applications.

European Journal of Medicinal Chemistry published new progress about Amidines Role: PAC (Pharmacological Activity), PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses) (hydroxyamidines). 658-99-1 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5F2N, Application of C8H5F2N.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Seelam, Preethi P.; Mitra, Abhijit; Sharma, Purshotam published the artcile< Pairing interactions between nucleobases and ligands in aptamer:ligand complexes of riboswitches: crystal structure analysis, classification, optimal structures, and accurate interaction energies>, COA of Formula: C7H5N5O, the main research area is nucleobases ligands riboswitches crystal structure.

In the present work, 67 crystal structures of the aptamer domains of RNA riboswitches are chosen for anal. of the structure and strength of hydrogen bonding (pairing) interactions between nucleobases constituting the aptamer binding pockets and the bound ligands. A total of 80 unique base:ligand hydrogen-bonded pairs containing at least two hydrogen bonds were identified through visual inspection. Classification of these contacts in terms of the interacting edge of the aptamer nucleobase revealed that interactions involving the Watson-Crick edge are the most common, followed by the sugar edge of purines and the Hoogsteen edge of uracil. Alternatively, classification in terms of the chem. constitution of the ligand yields five unique classes of base:ligand pairs: base:base, base:amino acid, base:sugar, base:phosphate, and base:other. This indicates that these contacts are well-defined RNA aptamer:ligand interaction motifs. The anal. was further extended to study the biol. importance of base:ligand interactions in the binding pocket of the tetrahydrofolate riboswitch and thiamine pyrophosphate riboswitch. Overall, our study helps in understanding the structural and energetic features of base:ligand pairs in riboswitches, which could aid in developing meaningful hypotheses in the context of RNA:ligand recognition. This can, in turn, contribute toward current efforts to develop antimicrobials that target RNAs.

RNA published new progress about Amino acids Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 69205-79-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C7H5N5O, COA of Formula: C7H5N5O.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Gharui, Chandan; Parida, Chandrakanta; Pan, Subhas Chandra published the artcile< Organocatalytic Asymmetric Addition of Aromatic α-Cyanoketones to o-Quinone Methides: Synthesis of 3,4-Dihydrocoumarins and Tetra-Substituted Chromans>, Computed Properties of 21667-62-9 , the main research area is acetylnitrile phenylsulfonylmethyl phenol organocatalyst enantioselective cycloaddition reaction; phenyldihydrocoumarin phenyl cyanochroman preparation.

The first organocatalytic asym. addition of aromatic α-cyanoketones to in situ- generated o-quinone methides was developed. The products 3,4-dihydrocoumarin and tetra-substituted chroman were obtained via bifunctional squaramide catalyzed conjugate addition reaction to in situ- generated o-quinone methides followed by treatment with 0.7 N HCl. With 10 mol % of the catalyst, the desired products were obtained in high enantio- and diastereoselectivities.

Journal of Organic Chemistry published new progress about [4+2] Cycloaddition reaction (stereoselective). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Computed Properties of 21667-62-9 .

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ma, Junlong; Chen, Heng; Yang, Jie; Yu, Zutao; Huang, Pan; Yang, Haofeng; Zheng, Bifeng; Liu, Rangru; Li, Qianbin; Hu, Gaoyun; Chen, Zhuo published the artcile< Binding pocket-based design, synthesis and biological evaluation of novel selective BRD4-BD1 inhibitors>, Computed Properties of 21667-62-9 , the main research area is neoplasm antitumor BRD4 BD1; BD1 inhibitor; BRD4; Cancer; Computer-aided drug design; Fibrosis; Structure-activity relationship.

Bromodomain-containing protein 4 (BRD4), consisting of two tandem bromodomains (BD1 and BD2), is key epigenetic regulator in fibrosis and cancer, which has been reported that BD1 and BD2 have distinct roles in post-translational modification. But there are few selective inhibitors toward those two domains. Herein, this study designed and synthesized a series of novel selective BRD4-BD1 inhibitors, using computer-aided drug design (CADD) approach focused on exploring the difference of the binding pockets of BD1 and BD2, and finding the His437 a crucial way to achieve BRD4-BD1 selectivity. Our results revealed that the compound 3u(I) is a potent selective BRD4-BD1 inhibitor with IC50 values of 0.56 μM for BD1 but >100 μM for BD2. I exhibited a broad spectrum of anti-proliferative activity against several human cancer and fibroblastic cell lines, which might be related to its capability of reducing the expression of c-Myc and collagen I. Furthermore, I could induce apoptosis in A375 cells. To the contrary, the selective BD2 inhibitor, RVX-208, did not indicate any of these activities. Our findings highlight that the function of BRD4-BD1 might be predominant in fibrosis and cancer. And it is rational to further develop novel selective BRD4-BD1 inhibitors.

Bioorganic & Medicinal Chemistry published new progress about Antitumor agents. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Computed Properties of 21667-62-9 .

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Gore, Babasaheb Sopan; Lin, Jun-Hao; Wang, Jeh-Jeng published the artcile< Unraveling innate substrate-controlled arylation and bicyclization of 1,5-enynes with α,β conjugates: synthesis of substituted benzo[a]fluorenes>, Category: nitriles-buliding-blocks, the main research area is enyne unsaturated ketone arylation arene cyclization Friedel Crafts; benzofluorene aryl regioselective preparation green chem.

A strategy for the aromatic C-H functionalization of electron-rich arenes, such as anisole, phenol, veratrol, toluene or naphthalene, with 1,5-enynes anchored by conjugates, e.g., I (X = CN, EtO2C, Ts, PhCO; R1 = n-Bu, Ph, 3-FC6H4, etc.; R2 = H, 4-Me, 5-F, 4-MeO, etc.; R3 = H, 4-Cl, 3-F, 3-Br, etc.) catalyzed by a Bronsted acid under metal- and solvent-free conditions has been developed. A diverse range of benzo[a]fluorenes, e.g., II [R4 = 4-MeOC6H4, 4-HOC6H4, 3,4-(MeO)2C6H3] [from I (X = CN)] or III (R4 = 4-MeOC6H4, 4-MeC6H4, 1-naphthyl), was obtained in moderate to good yields by using this protocol. This process includes intermol. nucleophilic arene insertion or 6-exo-dig cyclization (depending on the nature of the substrates) followed by a Friedel-Crafts-type reaction and 1,5-H transfer or intermol. nucleophilic arene insertion, resp. In addition, reactions with heterocyclic compounds such as (E)-2-benzoyl-3-(2-(phenylethynyl)pyridin-3-yl)acrylonitrile proceeded smoothly and afforded 11-phenyl-11H-indeno[1,2-h]quinoline-6-carbonitrile. Moreover, solvent recycling experiments were successfully carried out to illustrate green pathways. These reactions feature a readily accessible starting materials, transition metal-free approaches, simple one-pot operations, gram-scale syntheses and wide functional group tolerance.

Green Chemistry published new progress about Alkenynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

He, Zhonglei; Charleton, Clara; Devine, Robert W.; Kelada, Mark; Walsh, John M. D.; Conway, Gillian E.; Gunes, Sebnem; Mondala, Julie Rose Mae; Tian, Furong; Tiwari, Brijesh; Kinsella, Gemma K.; Malone, Renee; O’Shea, Denis; Devereux, Michael; Wang, Wenxin; Cullen, Patrick J.; Stephens, John C.; Curtin, James F. published the artcile< Enhanced pyrazolopyrimidinones cytotoxicity against glioblastoma cells activated by ROS-Generating cold atmospheric plasma>, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is pyrazolopyrimidinone cold atm plasma reactive oxygen species cytotoxicity; Cold atmospheric plasma; Glioblastoma; Pro-drug; Programmable cytotoxicity; Pyrazolopyrimidinone; ROS.

Pyrazolopyrimidinones are fused nitrogen-containing heterocyclic systems, which act as a core scaffold in many pharmaceutically relevant compounds Pyrazolopyrimidinones have been demonstrated to be efficient in treating several diseases, including cystic fibrosis, obesity, viral infection and cancer. In this study using glioblastoma U-251MG cell line, we tested the cytotoxic effects of 15 pyrazolopyrimidinones, synthesized via a two-step process, in combination with cold atm. plasma (CAP). CAP is an adjustable source of reactive oxygen and nitrogen species as well as other unique chem. and phys. effects which has been successfully tested as an innovative cancer therapy in clin. trials. Significantly variable cytotoxicity was observed with IC50 values ranging from around 11μM to negligible toxicity among tested compounds Interestingly, two pyrazolopyrimidinones were identified that act in a prodrug fashion and display around 5-15 times enhanced reactive-species dependent cytotoxicity when combined with cold atm. plasma. Activation was evident for direct CAP treatment on U-251MG cells loaded with the pyrazolopyrimidinone and indirect CAP treatment of the pyrazolopyrimidinone in media before adding to cells. Our results demonstrated the potential of CAP combined with pyrazolopyrimidinones as a programmable cytotoxic therapy and provide screened scaffolds that can be used for further development of pyrazolopyrimidinone prodrug derivatives

European Journal of Medicinal Chemistry published new progress about Antitumor agents. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Gharui, Chandan; Parida, Chandrakanta; Pan, Subhas Chandra published the artcile< Organocatalytic Asymmetric Addition of Aromatic α-Cyanoketones to o-Quinone Methides: Synthesis of 3,4-Dihydrocoumarins and Tetra-Substituted Chromans>, HPLC of Formula: 21667-62-9, the main research area is acetylnitrile phenylsulfonylmethyl phenol organocatalyst enantioselective cycloaddition reaction; phenyldihydrocoumarin phenyl cyanochroman preparation.

The first organocatalytic asym. addition of aromatic α-cyanoketones to in situ- generated o-quinone methides was developed. The products 3,4-dihydrocoumarin and tetra-substituted chroman were obtained via bifunctional squaramide catalyzed conjugate addition reaction to in situ- generated o-quinone methides followed by treatment with 0.7 N HCl. With 10 mol % of the catalyst, the desired products were obtained in high enantio- and diastereoselectivities.

Journal of Organic Chemistry published new progress about [4+2] Cycloaddition reaction (stereoselective). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, HPLC of Formula: 21667-62-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhong, De; Jiang, Feng; Shen, Siyong; Wang, Lan; Wang, Wei; Wu, Yongjun; Xiao, Yumei; Guo, Hongchao published the artcile< Formal [3+2] Annulation of Copper-Allenylidenes with 3-Oxo-3-Arylpropanenitriles: Synthesis of Tetrasubstituted Furans>, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is cyano methyl arylfuranyl phenyl methylbenzenesulfonamide preparation; ethynyl benzoxazinanone oxo arylpropanenitrile decarboxylative annulation copper catalyst.

The copper-catalyzed decarboxylative [3+2] annulation of ethynyl benzoxazinanones with 3-oxo-3-arylpropanenitriles was developed to produce tetrasubstituted furan derivatives I [R = Ph, 4-MeOC6H4, 4-pyridyl, etc.; R1 = H, 6-Me, 7-Cl, etc.] in moderate to high yield. This reaction was generally compatible with a wide range of substrates. Notably, the intermediate copper-allenylidenes worked as a C2 synthon in the cycloaddition reaction.

Advanced Synthesis & Catalysis published new progress about [3+2] Cycloaddition reaction. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts