Month: October 2022

Wei, Wen; Yu, Hao; Zangarelli, Agnese; Ackermann, Lutz published the artcile< Deaminative meta-C-H alkylation by ruthenium(II) catalysis>, COA of Formula: C9H7BrN2, the main research area is alkyl arene preparation chemoselective regioselective; heteroarene Katritzky pyridinium salt deaminative alkylation ruthenium catalyst.

A ruthenium-catalyzed meta-C-H deaminative alkylation with easily accessible amino acid-derived Katritzky pyridinium salts I (R = H, CO2Me, N-[(2S)-1-methoxy-1-oxopropan-2-yl]carbamoyl; R1 = CO2CH2CH3, CH2C6H5, 1H-indol-3-ylmethyl, etc.) has been described. Likewise, remote C-H benzylations were accomplished with high levels of chemoselectivity and remarkable functional group tolerance. The meta-C-H activation approach combined with the deaminative strategy represents a rare example of selectively converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds.

Chemical Science published new progress about Alkylation catalysts, regioselective (deaminative, chemoselective). 13788-92-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, COA of Formula: C9H7BrN2.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Jiang, Bo; Ning, Yi; Fan, Wei; Tu, Shu-Jiang; Li, Guigen published the artcile< Oxidative Dehydrogenative Couplings of Pyrazol-5-amines Selectively Forming Azopyrroles>, Quality Control of 118430-74-3, the main research area is stereoselective synthesis azopyrrole; oxidative dehydrogenative coupling pyrazolamine copper iodine.

New oxidative dehydrogenative couplings of pyrazol-5-amines for the selective synthesis of azopyrrole derivatives have been described. The reaction simultaneously installs C-I and N-N bonds through iodination and oxidation; a copper-catalyzed oxidative coupling process led to azopyrroles,. E.g., in presence of I2, TBHP, and K2CO3 in EtOH, dehydrogenative coupling of pyrazol-5-amine (I) gave 86% iodinated azopyrrole [(E)-II]. E.g., in presence of CuI, 1,10-phenanthroline, and TBHP in CH2Cl2, dehydrogenative coupling of I gave 56% (E)-III. The resulting iodo-substituted azopyrroles were employed by treatment with various terminal alkynes through Sonogashira cross-coupling leading to new azo compounds

Journal of Organic Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 118430-74-3 belongs to class pyrazoles-derivatives, and the molecular formula is C7H11N3, Quality Control of 118430-74-3.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Gutierrez, Corey D.; Bavetsias, Vassilios; McDonald, Edward published the artcile< ClTi(OiPr)3-Promoted Reductive Amination on the Solid Phase: Combinatorial Synthesis of a Biaryl-Based Sulfonamide Library>, Category: pyrazoles-derivatives, the main research area is combinatorial library biarylsulfonamide preparation; titanium promotor reductive amination aldehyde solid support; sulfonylation resin bound amine; sulfonamide biaryl combinatorial library preparation.

A combinatorial library (9 amines × 7 sulfonyl chlorides × 13 boronic acids = 819 compounds) was produced on solid support in a four-step sequence, i.e., ClTi(OiPr)3-promoted reductive amination, sulfonylation of the resin-bound amine, Suzuki cross-coupling, and acid-mediated cleavage. The library members (e.g. I) were obtained in moderate quantity (1-8 mg) with over 70% of the sampled products greater than 90% pure according to LC-MS anal.

Journal of Combinatorial Chemistry published new progress about Aldehydes Role: CMB (Combinatorial Study), RCT (Reactant), RACT (Reactant or Reagent). 936250-20-3 belongs to class pyrazoles-derivatives, and the molecular formula is C10H17BN2O2, Category: pyrazoles-derivatives.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Senga, Keitaro; O’Brien, Darrell E.; Scholten, Mieka B.; Novinson, Thomas; Miller, Jon P.; Robins, Roland K. published the artcile< Synthesis and enzymic activity of various substituted pyrazolo[1,5-a]-1,3,5-triazines as adenosine cyclic 3',5'-phosphate phosphodiesterase inhibitors>, COA of Formula: C6H5ClN4S, the main research area is pyrazolotriazine cAMP phosphodiesterase inhibitor preparation; pyrazolylamidine cyclization; amidine pyrazolyl cyclization.

I (R1 = H, Me, Et, SMe; R2 = H, Ph, Pr, SMe, NHEt, NHBu, NEt2 piperidino, OH, NHPr, SH, OCHMe2, Me, SEt, OMe, OPr; R3 = Ph, C6H4OMe-4, H; R4 = H, Br, C6H4Me-3, Ph, cyano, CO2Et, Cl), prepared by cyclizing II with (R2CO)2O or R2C(OEt)3, followed by electrophilic substitution in the pyrazole ring and/or nucleophilic substitution in the 1,3,5-triazine moiety, were studied as inhibitors of cAMP phosphodiesterase (PDE) isolated from bovine brain, bovine heart, and rabbit lung. A number of compounds were superior to theophylline. 2-Ethyl-7-phenylpyrazolo[1,5-a]-1,3,5-triazine was 97 times more potent than theophylline as an inhibitor of bovine brain PDE. 8-Bromo-2,4-dimethyl-7-phenylpyrazolo[1,5-a]-1,3,5-triazine showed αlung = 40 compared to αheart = 3.0. Thus, various substituents could increase or decrease the inhibition relative to the type and source of tissue from which the PDE was isolated. The most active compound was 8-bromo-4-(diethylamino)-7-phenylpyrazolo[1,5-a]-1,3,5-triazine which was 185 times more potent than theophylline as an inhibitor of PDE isolated from rabbit lung. Structure-activity relationships were reviewed.

Journal of Medicinal Chemistry published new progress about Structure-activity relationship. 54346-19-9 belongs to class pyrazoles-derivatives, and the molecular formula is C6H5ClN4S, COA of Formula: C6H5ClN4S.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Beveridge, Ramsay E.; Wallweber, Heidi Ackerly; Ashkenazi, Avi; Beresini, Maureen; Clark, Kevin R.; Gibbons, Paul; Ghiro, Elise; Kaufman, Susan; Larivee, Alexandre; Leblanc, Melissa; Leclerc, Jean-Philippe; Lemire, Alexandre; Ly, Cuong; Rudolph, Joachim; Schwarz, Jacob B.; Srivastava, Sanjay; Wang, Weiru; Zhao, Liang; Braun, Marie-Gabrielle published the artcile< Identification of BRaf-Sparing Amino-Thienopyrimidines with Potent IRE1α Inhibitory Activity>, Application In Synthesis of 1046832-21-6, the main research area is preparation BRaf amino thieno pyrimidine derivative IRE1 inhibitor cancer.

Amino-quinazoline BRaf kinase inhibitor 2 was identified from a library screen as a modest inhibitor of the unfolded protein response (UPR) regulating potential anticancer target IRE1α. A combination of crystallog. and conformational considerations were used to guide structure-based attenuation of BRaf activity and optimization of IRE1α potency. Quinazoline 6-position modifications were found to provide up to 100-fold improvement in IRE1α cellular potency but were ineffective at reducing BRaf activity. A salt bridge contact with Glu651 in IRE1α was then targeted to build in selectivity over BRaf which instead possesses a histidine in this position (His539). Torsional angle anal. revealed that the quinazoline hinge binder core was ill-suited to accommodate the required conformation to effectively reach Glu651, prompting a change to the thienopyrimidine hinge binder. Resulting analogs such as 25 demonstrated good IRE1α cellular potency and imparted more than 1000-fold decrease in BRaf activity.

ACS Medicinal Chemistry Letters published new progress about Antitumor agents. 1046832-21-6 belongs to class pyrazoles-derivatives, and the molecular formula is C11H19BN2O2, Application In Synthesis of 1046832-21-6.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Zhao, Yujun; Zhou, Bing; Bai, Longchuan; Liu, Liu; Yang, Chao-Yie; Meagher, Jennifer L.; Stuckey, Jeanne A.; McEachern, Donna; Przybranowski, Sally; Wang, Mi; Ran, Xu; Aguilar, Angelo; Hu, Yang; Kampf, Jeff W.; Li, Xiaoqin; Zhao, Ting; Li, Siwei; Wen, Bo; Sun, Duxin; Wang, Shaomeng published the artcile< Structure-Based Discovery of CF53 as a Potent and Orally Bioavailable Bromodomain and Extra-Terminal (BET) Bromodomain Inhibitor>, Synthetic Route of 118430-74-3, the main research area is pyrazole pyrimido indole preparation bromodomain inhibitor cancer.

We report the structure-based discovery of CF53 (28) as a highly potent and orally active inhibitor of bromodomain and extra-terminal (BET) proteins. By the incorporation of a NH-pyrazole group into the 9H-pyrimido[4,5-b]indole core, we identified a series of compounds that bind to BRD4 BD1 protein with Ki values of <1 nM and achieve low nanomolar potencies in the cell growth inhibition of leukemia and breast cancer cells. The most-promising compound, CF53, possesses excellent oral pharmacokinetic properties and achieves significant antitumor activity in both triple-neg. breast cancer and acute leukemia xenograft models in mice. Determination of the co-crystal structure of CF53 with the BRD4 BD1 protein provides a structural basis for its high binding affinity to BET proteins. CF53 is very selective over non-BET bromodomain-containing proteins. These data establish CF53 as a potent, selective, and orally active BET inhibitor, which warrants further evaluation for advanced preclin. development. Journal of Medicinal Chemistry published new progress about Antitumor agents. 118430-74-3 belongs to class pyrazoles-derivatives, and the molecular formula is C7H11N3, Synthetic Route of 118430-74-3.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Auwers, K. v.; Breyhan, Th. published the artcile< Further observations on alkylation and acylation of pyrazoles>, COA of Formula: C6H8N2O2, the main research area is .

3(5)- Methyl-5(3)-chloropyrazole with MeBr (8 hrs. at 100) gives 100% of the 1,3-di-Me derivative; CH2N2 gives largely the 1,3-di-Me derivative with some of the 1,5-isomer; the Na salt with Mel gives 100% of the 1,5-isomer. 3(5)- Phenylpyrazole (I) with MeBr (1 day at 100°) gives principally 1-methyl-3-phenylpyrazole, with some of the 5-Ph isomer; the Na salt with MeI yields 100% of the 5-Ph isomer. Excess ClCO2Me gives 1-carbomethoxy-3-phenylpyrazole (II), m. 76°. The Na derivative of BzCH:CHOH and MeO2CNHNH2 in dilute Et4OH give a nearly quant. yield of the carbomethoxyhydrazone of benzoylacetaldehyde, m. 152°; POCl3 in CHCl3 yields the 5-Ph isomer of II, m. 63-4°, with some II. I and SO2Cl2 give 4-chloro-5(3)- phenylpyrazole (III), b11 193°, m. 102°. 1-Methyl-4- chloro-3-phenylpyrazole (IV), pale brown, b9 163-5°; 5-Ph isomer (V), b12 153-6°. III and MeI with Na give about equal quantities of IV and V; Me2SO, in NaOH also give a mixture of the 2 isomers; MeBr gives essentially IV; CH2N2 reacts only slightly with III. II and SO2Cl2 give the 4-Cl derivative (VI), m. 89-90°; the 5-Ph isomer, m. 113-15°. III and ClCO2Me give VI. 3(5)-Methyl-5(3)-phenylpyrazole and MeBr (8 hrs. at 100°) give principally 1,5- dimethyl-3-phenylpyrazole, with some of the isomer; the Na salt with MeI gives the same products. 1-Carbomethoxy-3-phenyl-5-methylpyrazole, m. 74-5°; it is unchanged after heating with MeBr at 100° for 1 day; 4-Cl derivative, m. 107°. The carbomethoxyhydrazone of benzoylacetone, pale yellow, m. 121-2°; POCl3 gives 1-carbomethoxy-3-methyl-5-phenylpyrazole, m. 58-9°; 4-Cl derivative, m. 97°. Me pyrazole-3(5)-carboxylate, m. 139-40°; both MeBr and CH2N2 give principally Me 1-methylpyrazole-5-carboxylate, b9 73°, with a little of the 1,3-isomer, bg 120°. Me 5(3)-methylpyrazole-3(5)-carboxylate and CH2N2 give principally the 1,3-di-Me derivative, with some 1,5-isomer; the Et ester behaved similarly; there was no reaction with MeBr; MeI gives the almost pure 1,5-di- Me derivative; the Na salt with MeI gives principally the 1,3- isomer; EtI gives the 1-ethyl-5-methyl derivative; the salt with AcCl in C6H6 yields the 1-Ac derivative, m. 68.5-9.5°, and with ClCO2Me in Et2O the 1-MeO2C derivative Me 3(5)-phenylpyrazole-5(3)-carboxylate does not react with MeBr; with Mel it yields Me 1-methyl-3-phenylpyrazole 5-carboxylate; the Na salt and Mel in C6H6 give the same compound; the free ester or the Na salt and ClCO2Me yield a N-carbomethoxy derivative, m. 95°; the Et ester also does not react with EtBr; the Na salt and EtI give Et 1-ethyl-3- phenylpyrazole-5-carboxylate; the Na salt does not react with AcCl. 3(5)-Phenylpyrazole-5(3)-carboxylic acid (VII) and ClCO22Me give a N-carbomethoxy derivative, m. 126- 6.5°; with Cl the CO2Me group is split off. The 4-Cl derivative of VII m. 258-61°; it does not yield a CO2Me derivative

Journal fuer Praktische Chemie (Leipzig) published new progress about Acylation. 17827-61-1 belongs to class pyrazoles-derivatives, and the molecular formula is C6H8N2O2, COA of Formula: C6H8N2O2.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Broom, N. J. P.; Elder, J. S.; Hannan, P. C. T.; Pons, J. E.; O’Hanlon, P. J.; Walker, G.; Wilson, J.; Woodall, P. published the artcile< The chemistry of pseudomonic acid. Part 14. Synthesis and in vivo biological activity of heterocycle-substituted oxazole derivatives>, Electric Literature of 17827-61-1, the main research area is pseudomonic acid heterocycle oxazole derivative preparation; bactericide heterocycle oxazole derivative preparation.

Semisynthetic analogs of pseudomonic acid A were prepd containing a heterocycle-substituted oxazole. Derivatives in which the heterocycle was thiophene, furan, pyridine, or isoxazole showed good antibacterial potency and were further evaluated in vivo. Both pharmacokinetic parameters and oral activity against an exptl. i.p. sepsis were superior to results obtained from previously described pseudomonic acid A derivatives

Journal of Antibiotics published new progress about 17827-61-1. 17827-61-1 belongs to class pyrazoles-derivatives, and the molecular formula is C6H8N2O2, Electric Literature of 17827-61-1.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Dong, Xinrui; Jiang, Wenhua; Hua, Dexiang; Wang, Xiaohui; Xu, Liang; Wu, Xiaoxing published the artcile< Radical-mediated vicinal addition of alkoxysulfonyl/fluorosulfonyl and trifluoromethyl groups to aryl alkyl alkynes>, Safety of 1-(4-Bromophenyl)-1H-pyrazole, the main research area is trifluoromethylalkenylsulfonate ester sulfonyl fluoride preparation diastereoselective; aryl alkyl alkyne alkoxy fluorosulfonyl trifluoromethylation radical mediator.

The addition of sulfonyl radicals to alkenes and alkynes is a valuable method for constructing useful highly functionalized sulfonyl compounds The underexplored alkoxy- and fluorosulfonyl radicals are easily accessed by CF3 radical addition to readily available allylsulfonic acid derivatives and then β-fragmentation. These substituted sulfonyl radicals add to aryl alkyl alkynes to give vinyl radicals that are trapped by trifluoromethyl transfer to provide tetra-substituted alkenes bearing the privileged alkoxy- or fluorosulfonyl group on one carbon and a trifluoromethyl group on the other. This process exhibits broad functional group compatibility and allows for the late-stage functionalization of drug mols., demonstrating its potential in drug discovery and chem. biol. And alkyl allylsulfonates/allylsulfonyl fluoride.

Chemical Science published new progress about Alkynes, aryl Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (alkyl). 13788-92-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, Safety of 1-(4-Bromophenyl)-1H-pyrazole.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Perrocheau, Jacques; Carrie, Robert; Fleury, Jean-Pierre published the artcile< Thermal and photochemical evolution of triazolines obtained by addition of diazo compounds to methyl esters of oximino-malonodinitriles, oximino-cyanoacetates and oximino-malonates>, HPLC of Formula: 17827-61-1, the main research area is thermolysis triazoline; photolysis triazoline; triazoline thermolysis photolysis; aziridine.

Thermolysis of 1,2,3-triazolines I [R = Ts, COC6H4Z-4, Ac; R1 = H, Me, Ph, (MeO)2CH] leads to the corresponding aziridines only when X = Y = CO2Me, and then with a very low yield. However, photolysis or evolution in the presence of trifluoroacetic acid gives good results when carried out at sufficiently low temperature The thermolysis study of I shows a new route to 1,2,3-triazoline decomposition that has not yet been mentioned in the literature. The easy elimination of the p-toluenesulfonate or benzoate group explains this particular behavior.

Canadian Journal of Chemistry published new progress about Photolysis. 17827-61-1 belongs to class pyrazoles-derivatives, and the molecular formula is C6H8N2O2, HPLC of Formula: 17827-61-1.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics