Tag: M.W=200-250

Wang, Tao; Wang, Yi-Ning; Wang, Rui; Zhang, Bo-Chao; Yang, Chi; Li, Yan-Lin; Wang, Xi-Sheng published the artcile< Enantioselective cyanation via radical-mediated C-C single bond cleavage for synthesis of chiral dinitriles>, Safety of 3-Bromobenzotrifluoride, the main research area is chiral dinitrile enantioselective preparation; cycloalkanone oxime ester enantioselective cyanation copper catalyst.

Herein, radical-mediated ring-opening and enantioselective cyanation of four- and five-membered cycloketone oxime esters was described to access chiral 1,5- and 1,6-dinitriles ArCHCN(CH2)nCN [R = Ph, 1-naphthyl, 2-naphthyl, etc.; n = 2, 3] with R-stereochem. Employment of dual photoredox/copper catalysis was essential for the asym. ring-opening cyanation of cyclopentanone oxime esters. Both reactions proceeded under mild conditions giving chiral dinitriles in high yields and enantioselectivity with low catalyst loading and broad substrate scope. The products dinitriles could be converted to valuable optically active diamides and diamines. Mechanistic studies indicate that the benzylic radical generated via C-C single bond cleavage was involved in the catalytic cycle.

Nature Communications published new progress about C-C bond cleavage. 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Safety of 3-Bromobenzotrifluoride.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Kozikowski, Alan P.; Shen, Sida; Pardo, Marta; Tavares, Mauricio T.; Szarics, Dora; Benoy, Veronick; Zimprich, Chad A.; Kutil, Zsofia; Zhang, Guiping; Barinka, Cyril; Robers, Matthew B.; Van Den Bosch, Ludo; Eubanks, James H.; Jope, Richard S. published the artcile< Brain Penetrable Histone Deacetylase 6 Inhibitor SW-100 Ameliorates Memory and Learning Impairments in a Mouse Model of Fragile X Syndrome>, Computed Properties of 128577-47-9, the main research area is Phenylhydroxamate permeability Ames neg acetylated memory and learning impairments; Ames negative; Phenylhydroxamate; acetylated α-tubulin; memory and learning impairments; permeability.

Disease-modifying therapies are needed for Fragile X Syndrome (FXS), as at present there are no effective treatments or cures. Herein, we report on a tetrahydroquinoline-based selective histone deacetylase 6 (HDAC6) inhibitor SW-100, its pharmacol. and ADMET properties, and its ability to improve upon memory performance in a mouse model of FXS, Fmr1-/- mice. This small mol. demonstrates good brain penetrance, low-nanomolar potency for the inhibition of HDAC6 (IC50 = 2.3 nM), with at least a thousand-fold selectivity over all other class I, II, and IV HDAC isoforms. Moreover, through its inhibition of the α-tubulin deacetylase domain of HDAC6 (CD2), in cells SW-100 upregulates α-tubulin acetylation with no effect on histone acetylation and selectively restores the impaired acetylated α-tubulin levels in the hippocampus of Fmr1-/- mice. Lastly, SW-100 ameliorates several memory and learning impairments in Fmr1-/- mice, thus modeling the intellectual deficiencies associated with FXS, and hence providing a strong rationale for pursuing HDAC6-based therapies for the treatment of this rare disease.

ACS Chemical Neuroscience published new progress about Blood-brain barrier. 128577-47-9 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8BrFO2, Computed Properties of 128577-47-9.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhou, Haiping; Jiang, Junhao; Lu, Jinyu; Ran, Dongzhi; Gan, Zongjie published the artcile< Synthesis and biological evaluation of novel 2,4-dianilinopyrimidine derivatives as potent dual janus kinase 2 and histone deacetylases inhibitors>, Product Details of C7H4BrF3, the main research area is dianilinopyrimidine preparation janus kinase histone deacetylase inhibitor antitumor docking; tert butyl chloro pyrimidinyl amino benzenesulfonamide preparation; phenyl bromide chloro pyrimidinyl amine Buchwald Hartwig.

Herein, a novel series of 2,4-dianilinopyrimidine derivatives, I [R1 = 3-SO2NHC(CH3)3, 3-F, 3-SO2NHCH(CH3)2, etc.; R2 = H, Me; n = 0, 3, 5, 6] was presented which could simultaneously inhibit JAK2 and HDAC1. Among which, I [R1 = 3-OMe, R2 = Me, n = 6] was found to be the most potent compound and displayed balanced inhibitory activity against HDAC1 (IC50 = 1.9 nM) and JAK2 (IC50 = 0.5 nM), resp. [R1 = 3-OMe, R2 = Me, n = 6] also demonstrated good antiproliferative activity against tested cancer cell lines (A549, HepG-2, MDA-MB-231 and Jurkat). Moreover, flow cytometric anal. showed that I [R1 = 3-OMe, R2 = Me, n = 6] induced apoptosis and cell cycle arrest in a dose-dependent manner, and the insight into mechanisms of I [R1 = 3-OMe, R2 = Me, n = 6] indicated that it could decrease the phosphorylation of STAT-3 and promote histone acetylation. In conclusion, these results together suggested that I [R1 = 3-OMe, R2 = Me, n = 6] would be a promising lead candidate and deserved further research and development.

Journal of Molecular Structure published new progress about Antiproliferative agents. 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Product Details of C7H4BrF3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Kim, Ju-Hye; Park, Eun-Jin; Lee, Hwa-Jung; Ho, Xuan-Huong; Yoon, Hyo-Sang; Kim, Pilsoo; Yun, Hoseop; Jang, Hye-Young published the artcile< Tandem Iminium/Copper Catalysis: Highly Enantioselective Synthesis of α,β-Disubstituted Aldehydes>, COA of Formula: C9H7BrO, the main research area is iminium copper catalyst enantioselective aldehyde Michael addition.

With the goal of synthesizing biol. and synthetically valuable products under environmentally benign and economic conditions, an asym. organocatalytic reaction was combined with a copper catalytic reaction. This iminium/copper catalysis allowed highly optically active α,β-disubstituted aldehydes to be synthesized with good yields in one-pot fashion. The β-substitution took place through iminium-catalyzed Michael addition of nitromethane or di-Et malonate to the α,β-unsaturated aldehydes, followed by copper-assisted addition of TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxyl) at the aldehyde α-position. An iminium/copper-catalyzed tandem addition product was converted into a 3,4,5-trisubstituted piperidine for x-ray crystallog. anal.

European Journal of Organic Chemistry published new progress about Crystal structure. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, COA of Formula: C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Jiang, Sheng-Peng; Dong, Xiao-Yang; Gu, Qiang-Shuai; Ye, Liu; Li, Zhong-Liang; Liu, Xin-Yuan published the artcile< Copper-Catalyzed Enantioconvergent Radical Suzuki-Miyaura C(sp3)-C(sp2) Cross-Coupling>, Application of C8H8BrF, the main research area is diarylalkane arylalkyne enantioselective preparation; copper catalyst enantioselective Suzuki Miyaura coupling benzylic propargyl bromide; acenaphthylenediolboronate enantioselective Suzuki Miyaura coupling benzylic propargyl bromide; radical mechanism copper catalyzed enantioselective Suzuki Miyaura coupling.

A copper-catalyzed enantioconvergent Suzuki-Miyaura C(sp3)-C(sp2) cross-coupling of various racemic alkyl halides with organoboronate esters has been established in high enantioselectivity. Critical to the success is the use of a chiral cinchona alkaloid-derived N,N,P-ligand for not only enhancing the reducing capability of copper catalyst to favor a stereoablative radical pathway over a stereospecific SN2-type process but also providing an ideal chiral environment to achieve the challenging enantiocontrol over the highly reactive radical species. The reaction has a broad scope with respect to both coupling partners, covering aryl- and heteroarylboronate esters, as well as benzyl-, heterobenzyl-, and propargyl bromides and chlorides with good functional group compatibility. Thus, it provides expedient access toward a range of useful enantioenriched skeletons featuring chiral tertiary benzylic stereocenters.

Journal of the American Chemical Society published new progress about Alkynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (aralkyl). 405931-46-6 belongs to class bromides-buliding-blocks, and the molecular formula is C8H8BrF, Application of C8H8BrF.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Maddirala, Amarendar Reddy; Klein, Roger; Pinkner, Jerome S.; Kalas, Vasilios; Hultgren, Scott J.; Janetka, James W. published the artcile< Biphenyl Gal and GalNAc FmlH Lectin Antagonists of Uropathogenic E. coli (UPEC): Optimization through Iterative Rational Drug Design>, Related Products of 135999-16-5, the main research area is galactoside biphenyl preparation FmlH lectin antagonist UPEC urinary infection; galactosaminoside biphenyl preparation FmlH lectin antagonist UPEC urinary infection.

The F9/Yde/Fml pilus, tipped with the FmlH adhesin, has been shown to provide uropathogenic Escherichia coli (UPEC) a fitness advantage in urinary tract infections (UTIs). Here, the authors used X-ray structure guided design to optimize our previously described ortho-biphenyl Gal and GalNAc FmlH antagonists by replacing the carboxylate with a sulfonamide. Other groups which can accept H-bonds were also tolerated. The authors pursued further modifications to the biphenyl aglycon resulting in significantly improved activity. Two of the most potent compounds (IC50 = 0.051 μM) and (IC50 = 0.034 μM), exhibited excellent metabolic stability in mouse plasma and liver microsomes but showed only limited oral bioavailability (<1%) in rats. Another compound also showed a good pharmacokinetic (PK) profile in mice after IP dosing with compound exposure above the IC50 for 6 h. These new FmlH antagonists represent new antivirulence drugs for UTIs. Journal of Medicinal Chemistry published new progress about Drug design. 135999-16-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H7BrO2, Related Products of 135999-16-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ma, Yuanyuan; Gao, Qianwen; Zhou, Lan; Liu, Shanshan; Cheng, Hong-Gang; Zhou, Qianghui published the artcile< Diversity-Oriented Synthesis of Flavones and Isoflavones via Palladium/Norbornene Cooperative Catalysis>, COA of Formula: C8H6BrFO2, the main research area is arylated chromone chemoselective preparation; iodochromone aryl bromide olefin Heck palladium catalyst norbornene; potassium trifluoroborate iodochromone aryl bromide Suzuki palladium catalyst norbornene; alkylating reagent potassium trifluoroborate iodochromone alkylation palladium catalyst norbornene.

Diversity-oriented synthesis of arylated chromones I [R = H, 6-F, 7-Cl, etc.; R1 = CH=CHC6H5, Ph, 2-thienyl, etc.; R2 = Me, 2-NO2C6H4, 2-CO2MeC6H4, etc.] from 3-iodochromones via palladium/norbornene cooperative catalysis was reported. The success of this research reliesd on the use of a unique bridge-head ester modified norbornene derivative as the mediator. Salient features of this include readily available starting materials regarding 3-iodochromones, ortho-C-H arylating and alkylating reagents and ipso-terminating reagents, broad substrate scope, good chemoselectivity, good step-economy and scalability. A large number of structurally diversified flavones, isoflavones and 2,3-diarylated chromones could be quickly prepared in a predictable manner. As showcased by the efficient formal synthesis of umbralisib, this chem. could be treated as another valuable addition to the toolbox of medicinal chemists.

Chinese Journal of Chemistry published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 6942-39-8 belongs to class bromides-buliding-blocks, and the molecular formula is C8H6BrFO2, COA of Formula: C8H6BrFO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Chen, Lian-Mei; Zhao, Juan; Xia, An-Jie; Guo, Xiao-Qiang; Gan, Ya; Zhou, Chuang; Yang, Zai-Jun; Yang, Jun; Kang, Tai-Ran published the artcile< A base-promoted cascade reaction of α,β-unsaturated N-tosylhydrazones with o-hydroxybenzyl alcohols: highly regioselective synthesis of N-sec-alkylpyrazoles>, HPLC of Formula: 3893-18-3, the main research area is hydroxymethyl arylalc arylethenyl tosylhydrazone base tandem heterocyclization aza Michael; arylpyrazolylmethyl aryl alc preparation regioselective.

An efficient method for the synthesis of N-sec-alkylpyrazoles through a base-promoted cascade cyclization/Michael addition reaction of α,β-unsaturated N-tosylhydrazones with ortho-hydroxybenzyl alcs. was developed. The desired products containing di- or triaryl groups at the same carbon atom were afforded in good to excellent yields with excellent regioselectivities (>20 : 1). Moreover, a three-component reaction of ortho-hydroxybenzyl alcs., α,β-unsaturated N-tosylhydrazones and saturated N-tosylhydrazones also took place to afforded pyrazoles in good yields. This reaction offered a new route to triarylmethanes with a simple operation and was applicable for large-scale synthesis.

Organic & Biomolecular Chemistry published new progress about Alkylarenes Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, HPLC of Formula: 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Qiao, Lulin; Zhang, An-An; Chen, Jingchao; Li, Gao-Wei; Gao, Yuan-Yuan; Fan, Baomin; Liu, Lantao published the artcile< Palladium-catalyzed disilylation of 2-bromoarylferrocenes: An efficient approach to 1-Trimethylsilyl-2-(2-trimethylsilylaryl)ferrocenes>, Quality Control of 51605-97-1, the main research area is crystal structure mol disilylated ferrocene preparation; palladium catalyst disilylation bromoaryl ferrocene mechanism.

An unprecedented method for the palladium-catalyzed disilylation of 2-bromoarylferrocenes with hexamethyldisilane has been developed. The catalytic cycle is initiated by oxidative addition of 2-bromoarylferrocenes to Pd(0), followed by C-H activation to form a reactive five-membered C,C-palladacycle. By using this protocol, a variety of disilylated ferrocene compounds were obtained in moderate to good yields.

Tetrahedron Letters published new progress about C-H bond activation. 51605-97-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H12BrN, Quality Control of 51605-97-1.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

He, Zhao-Quan; Zhou, Quan; Wu, Li; Chen, Ying-Chun published the artcile< Asymmetric organocatalytic tandem reaction to chiral pyrimidinone derivatives using urea as dinitrogen source>, Synthetic Route of 3893-18-3, the main research area is substituted pyrimidinone derivative asym preparation; urea unsaturated aldehyde cyclocondensation chiral amines.

A facile method for the asym. synthesis of pyrimidinone derivatives was developed via an organocatalytic tandem aza-Michael addition-hemiaminal formation-dehydroxylation reaction, using N,N’-dialkyloxyurea as dinitrogen source (up to 97% ee). The transformations of hemiaminal intermediates to pyrimidinones with more complex structures have been also investigated.

Advanced Synthesis & Catalysis published new progress about Amines, chiral Role: CAT (Catalyst Use), USES (Uses). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Synthetic Route of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary