Tag: M.W=200-250

Shen, Yanling; Lei, Ning; Lu, Cong; Xi, Dailin; Geng, Xinxin; Tao, Pan; Su, Zhishan; Zheng, Ke published the artcile< Construction of sterically congested oxindole derivatives via visible-light-induced radical-coupling>, Related Products of 401-78-5, the main research area is oxindole preparation antitumor photochem; alkene enyne oxindole radical coupling reaction.

A visible-light-induced modular methodol. for the synthesis of complex 3,3′-disubstituted oxindole derivatives, e.g. I, is reported. A library of valuable fluoroalkyl-containing highly sterically congested oxindole derivatives can be synthesized by a catalytic three-component radical coupling reaction under mild conditions (metal and photocatalyst free, >80 examples). This strategy shows high functional group tolerance and broad substrate compatibility. Substrates include a wide variety of terminal or non-terminal alkenes, conjugated dienes (e.g. prop-1-en-2-ylbenzene), and enynes RC(:CH2)CCR1 (R = Me, Ph, R1 = H, Ph, cyclopropyl, 3-chloropropyl), and a broad array of polyfluoroalkyl iodide and oxindoles II (R2 = 7-Cl, 5-Br, 4,6-F2, etc., R3 = Ph, 5-methylthiophen-2-yl, 6-methoxynaphthalen-1-yl, etc.), which enables modular modification of complex drug-like compounds in one chem. step. The success of solar-driven transformation, large-scale synthesis, and the late-stage functionalization of bioactive mols., as well as promising tumor-suppressing biol. activities, highlights the potential for practical applications of this strategy. Mechanistic investigations, including a series of control experiments, UV-vis spectroscopy and DFT calculations, suggest that the reaction underwent a sequential two-step radical-coupling process and the photosensitive perfluoroalkyl benzyl iodides are key intermediates in the transformation.

Chemical Science published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Related Products of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wan, Lin-Xi; Zhen, Yong-Qi; He, Zhen-Xiang; Zhang, Yang; Zhang, Lan; Li, Xiaohuan; Gao, Feng; Zhou, Xian-Li published the artcile< Late-Stage Modification of Medicine: Pd-Catalyzed Direct Synthesis and Biological Evaluation of N-Aryltacrine Derivatives>, Application In Synthesis of 401-78-5, the main research area is tacrine aryl preparation Buchwald Hartwig cross coupling palladium catalyst; cholinesterase inhibitor aryltacrine; hepatotoxicity aryltacrine; neuroprotective aryltacrine; mol docking methoxypyridinyl tacrine acetylcholinesterase butyrylcholinesterase; blood brain barrier permeability aryltacrine.

A new series of N-aryltacrine derivatives was designed and synthesized as cholinesterase inhibitors by the late-stage modification of tacrine, using the palladium-catalyzed Buchwald-Hartwig cross-coupling reaction. In vitro inhibition assay against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) demonstrated that most of the synthesized compounds had potent AChE inhibitory activity with neg. inhibition of BuChE. Among them, N-(4-(trifluoromethyl)phenyl)-tacrine (I) and N-(4-methoxypyridin-2-yl)-tacrine (II) showed the most potent activity against AChE (IC50 values of 1.77 and 1.48μM, resp.). The anti-AChE activity of I and II was 3.5 times more than that of tacrine (IC50 value of 5.16μM). Compound II also displayed anti-BuChE activity with an IC50 value of 19.00μM. Cell-based assays against HepG2 and SH-SY5Y cell lines revealed that II had significantly lower hepatotoxicity compared to tacrine, with addnl. neuroprotective activity against H2O2-induced damage in SH-SY5Y cells. The advantages including synthetic accessibility, high potency, low toxicity, and adjunctive neuroprotective activity make compound II a new promising multifunctional candidate for the treatment of Alzheimer’s disease.

ACS Omega published new progress about Alzheimer disease. 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Application In Synthesis of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Bookser, Brett C.; Kasibhatla, Srinivas Rao; Appleman, James R.; Erion, Mark D. published the artcile< AMP Deaminase Inhibitors. 2. Initial Discovery of a Non-Nucleotide Transition-State Inhibitor Series>, SDS of cas: 14062-30-7, the main research area is coformycin aglycon analog preparation AMPDA inhibitor; adenylate adenosine deaminase inhibitor coformycin analog.

A series of N3-substituted coformycin aglycon analogs are described that inhibit AMP deaminase (AMPDA) or adenosine deaminase (ADA). The key steps involved in the preparation of these compounds are treating the sodium salt of 6,7-dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one with an alkyl bromide or an alkyl mesylate to generate the N3-alkylated compound, and (2) reducing the N3-alkylated compound with NaBH4. Selective inhibition of AMPDA was realized when the N3-substituent contained a carboxylic acid moiety. For example, the compound which has a hexanoic acid side chain inhibited AMPDA with a Ki = 4.2 μM and ADA with a Ki = 280 μM. Substitution of large lipophilic groups α to the carboxylate provided a moderate potency increase with maintained selectivity as exemplified by the α-benzyl analog (AMPDA Ki = 0.41 μM and ADA Ki > 1000 μM). These compounds, as well as others described in this series of papers, are the first compounds suitable for testing whether selective inhibition of AMPDA can protect tissue from ischemic damage by increasing local adenosine concentrations at the site of injury and/or by minimizing adenylate loss.

Journal of Medicinal Chemistry published new progress about Structure-activity relationship, enzyme-inhibiting. 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, SDS of cas: 14062-30-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Lu, Dehua; Qu, Lailiang; Wang, Cheng; Luo, Heng; Li, Shang; Yin, Fucheng; Liu, Xingchen; Chen, Xinye; Luo, Zhongwen; Cui, Ningjie; Peng, Wan; Ji, Limei; Kong, Lingyi; Wang, Xiaobing published the artcile< Harmine-based dual inhibitors targeting histone deacetylase (HDAC) and DNA as a promising strategy for cancer therapy>, SDS of cas: 85070-57-1, the main research area is cancer therapy histone deacetylase harmine DNA damage; Cancer; DNA; DNA damage; HDAC; Harmine.

Overexpression of histone deacetylases (HDACs) are observed in different types of cancers, but histone deacetylase inhibitors (HDACIs) have not shown significant efficacy as monotherapy against solid tumors. Recently, studies demonstrated that it is promising to combine HDACIs with DNA damage agents to improve DNA damage level to gain better effect on treating solid tumor. Harmine has been demonstrated to cause DNA damage by intercalating DNA. Therefore, we designed a series of harmine-based inhibitors targeting HDAC and DNA with multi-target strategy, the most potential compound 27 could bind to DNA and cause DNA damage. Furthermore 27 caused cells apoptosis through p53 signaling pathway, and exhibited significant anti-proliferation effects against HCT-116 cells (IC50 = 1.41 μM). As a DNA damage agent, 27 displayed low toxicity in normal cells. Compound 27 was demonstrated as a dual inhibitor targeting HDAC (HDAC1 IC50 = 0.022 μM and HDAC6 IC50 = 0.45 μM) and DNA, and had the potential in the treatment of solid tumor.

Bioorganic Chemistry published new progress about Acetylation. 85070-57-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8BrFO2, SDS of cas: 85070-57-1.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sunden, Henrik; Rios, Ramon; Ibrahem, Ismail; Zhao, Gui-Ling; Eriksson, Lars; Cordova, Armando published the artcile< A highly enantioselective catalytic domino aza-Michael/aldol reaction: one-pot organocatalytic asymmetric synthesis of 1,2-dihydroquinolines>, Application of C9H7BrO, the main research area is stereoselective Michael aldol aminobenzaldehyde unsaturated aldehyde catalyst.

The highly enantioselective organocatalytic domino aza-Michael/aldol reaction is presented. The unprecedented, chiral amine-catalyzed asym. domino reactions between 2-aminobenzaldehydes and α,β-unsaturated aldehydes proceed with excellent chemo- and enantioselectivity to give the corresponding pharmaceutically valuable 1,2-dihydroquinolines in high yields with 90 to > 99 % ee.

Advanced Synthesis & Catalysis published new progress about Aldol condensation catalysts, stereoselective. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Application of C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Chen, Jinglei; Hu, Hang; Ye, Kai; Wang, Wei; Xu, Defeng published the artcile< Synthesis of Novel Pyrimidinylselenium Compounds as Acetolactate Synthase-Inhibiting Herbicides>, Category: bromides-buliding-blocks, the main research area is Eleusine Amaranthus Portulaca pyrimidinylselenium acetolactate synthase herbicide.

A series of pyrimidinylselenosalicylic acid derivatives (5 a-5 l) and 4-selenopyrimidine derivatives (6 a-6 f) were synthesized and evaluated as potential acetylactate synthase (ALS)-inhibiting herbicides. All synthesized new compounds were characterized by 1H NMR, 13C NMR, and high-resolution mass spectrometry (HRMS). The compounds were subjected to herbicidal activity, in vitro ALS enzyme inhibitory activity, and crop safety studies. The herbicidal activity study shows that 4-chloro (5 b), 5-chloro (5 c), 5-methoxy (5 e), 4,5-dimethoxy (5 f), 5-fluoro (5 h), and 4,5-difluoro (5 i) substituted 2-[(4,6-dimethoxy-2-pyrimidinyl)selanyl]benzoic acid exhibit significantly enhanced weed control effect than other new compounds and Pyrithiobac. Most of compounds exhibit enhanced inhibition effect on Cyperus difformis Linn than those on barnyard grass, Portulaca oleracea, Eleusine indica, and Amaranthus retroflexus. Importantly, 5 c, 5 f, and 5 i also exhibit more potent inhibition effect on Escherichia coli ALS enzyme than other new compounds and Pyrithiobac in in vitro ALS enzyme inhibitory activity study. The possible binding modes of 5 c, 5 f, and 5 i with ALS enzyme were studied on Discovery Studio. To test the possibility of 5 c, 5 f, and 5 i as potential herbicides in paddy fields, we performed the crop safety study. The results show that 5 f and 5 i are safer to rice than 5 c. The present work indicates that 5 f and 5 i may serve as new herbicide candidates for weed control in paddy fields.

ChemistrySelect published new progress about Affinity (binding). 20776-50-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H6BrNO2, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Luo, Jiaying; Lu, Youling; Liu, Saiwen; Liu, Jing; Deng, Guo-Jun published the artcile< Efficient One-Pot Synthesis of Dibenzopyranones via a Decarboxylative Cross-Coupling and Lactonization Sequence>, Safety of Methyl 2-bromo-5-fluorobenzoate, the main research area is dibenzopyranone preparation decarboxylative coupling lactonization halobenzoate nitrobenzoic acid; copper palladium catalyst decarboxylative coupling lactonization halobenzoate nitrobenzoic acid.

A highly selective palladium bis(acetoacetonate)/copper(I) chloride [Pd(acac)2/CuCl] catalytic system for the preparation of dibenzopyranones has been developed. Tandem decarboxylative coupling and lactonization can be realized in one pot using com. available starting materials. The reaction proceeded well for a range of different substrates.

Advanced Synthesis & Catalysis published new progress about Aromatic carboxylic acids Role: RCT (Reactant), RACT (Reactant or Reagent) (nitro-). 6942-39-8 belongs to class bromides-buliding-blocks, and the molecular formula is C8H6BrFO2, Safety of Methyl 2-bromo-5-fluorobenzoate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Uryu, Mizuho; Hiraga, Taito; Koga, Yoshito; Saito, Yutaro; Murakami, Kei; Itami, Kenichiro published the artcile< Synthesis of Polybenzoacenes: Annulative Dimerization of Phenylene Triflate by Twofold C-H Activation>, Computed Properties of 81107-97-3, the main research area is polybenzoacene preparation; phenylene triflate preparation annulative dimerization palladium catalyst; C−H activation; annulations; fused rings; palladium; polycycles.

Polycyclic aromatic hydrocarbons (PAHs) represent an emerging class of π-conjugated mols. in the area of optoelectronic devices and materials. Unprecedented synthetic routes to various PAHs from simple phenol derivatives by a palladium-catalyzed annulative dimerization of phenylene triflate through twofold inter- and intramol. C-H activation have been established. The initially formed partially fused PAHs can be smoothly transformed into a variety of fully fused PAHs by the Scholl reaction. Furthermore, the reactions of phenanthrene-substituted aryl triflates proceeded regioselectively. The findings inspired the development of a rapid and efficient synthesis of polybenzoacene derivatives This study not only allows transformation of Ph triflates, but also discloses a new retrosynthetic strategy towards PAHs, especially polybenzoacenes.

Angewandte Chemie, International Edition published new progress about C-H bond activation. 81107-97-3 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3O, Computed Properties of 81107-97-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Yu, Han; Dai, Guoyong; He, Qiu-Rui; Tang, Jiang-Jiang published the artcile< Enantioselective synthesis and evaluation of 4-styryldihydropyrimidin-2-thiones as anti-proliferative agents>, Reference of 3893-18-3, the main research area is styryldihydropyrimidinethione preparation enantioselective anticancer; cinnamaldehyde thiourea ketoester Biginelli reaction organocatalyst.

A series of novel chiral (S)-4-styryldihydropyrimidin-2-thiones I (R1 = H, F, NO2, etc.; R2 = i-Pr, t-Bu; R3 = Me, Et) was prepared with high yields and enantioselective by a Biginelli reaction. In the condensation reaction, substituted cinnamaldehyde R1C6H4CH=CHCHO, thiourea and β-ketoesters R2C(O)CH2C(O)2R3 were organocatalyzed to afford 4-styryldihydropyrimidin-2-thiones I using self-assembled methanoproline-thiourea as catalysts. Anti-proliferative activity of these 4-styryldihydropyrimidin-2-thiones I was tested against the HepG2 and PC-3 cells. Among all the tested compounds, I (R1 = CF3; R2 = i-Pr, t-Bu; R3 = Me, Et) bearing CF3- groups at styryl group displayed a moderate anti-proliferative activity with IC50 ranged between 29.3-38.5 μM. The structure-activity relationship showed that substituents (R1) on the C-4 styryl ring of 4-styryldihydropyrimidin-2-thiones and R3 at ester group affected the anti-proliferative activity, yet R2 at C-6 position had little influence for anti-proliferative activity.

Medicinal Chemistry Research published new progress about Antitumor agents. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Reference of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

He, Min; Yu, Xiaoqiang; Wang, Yi; Bao, Ming published the artcile< Tunable redox potential photocatalyst: aggregates of 2,3-dicyanopyrazino phenanthrene derivatives for the visible-light-induced α-allylation of amines>, Related Products of 401-78-5, the main research area is photocatalysis photoredox alpha allylation phenanthrene pi stacking.

This work highlights the tunable redox potential of 6,11-dibromo-2,3-dicyanopyrazinophenanthrene (DCPP3) aggregates, which can be formed through phys. π-π stacking interactions with other DCPP3 monomers. Electrochem. and SEM showed that the reduction potential of [DCPP3]n aggregates could be increased by decreasing their size. The size of [DCPP3]n aggregates could be regulated by controlling the concentration of DCPP3 in an organic solvent. As such, a fundamental understanding of this tunable redox potential is essential for developing new materials for photocatalytic applications. The [DCPP3]n aggregates as a visible-light photocatalyst in combination with Pd catalysts in the visible-light-induced α-allylation of amines were used. This [DCPP3]n photocatalyst exhibits excellent photo- and electrochem. properties, including a remarkable visible-light absorption, long excited-state lifetime (16.6μs), good triplet quantum yield (0.538), and high reduction potential (Ered([DCPP3]n/[DCPP3]n-) > -1.8 V vs SCE).

Journal of Organic Chemistry published new progress about Allylation. 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Related Products of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary