Tag: M.W=200-250

Leng, Haijun; Zhao, Qian; Mao, Qing; Liu, Shuaijiang; Luo, Menglan; Qin, Rui; Huang, Wei; Zhan, Gu published the artcile< NHC-catalysed retro-aldol/aldol cascade reaction enabling solvent-controlled stereodivergent synthesis of spirooxindoles>, Recommanded Product: 3-(4-Bromophenyl)acrylaldehyde, the main research area is spirocyclopentaneoxindole preparation diastereo enantioselective solvent controlled stereodivergent NHC catalyst; oxindole unsaturated aldehyde Michael retro aldol tandem reaction.

An N-heterocyclic carbene (NHC)-catalyzed retro-aldol/aldol cascade reaction of spirooxindole-based β-hydroxyaldehydes has been developed. The ring opening-closure process enables the diastereodivergent synthesis of spirocyclopentaneoxindole products I (R’ = Bn, allyl; R1 = H, 5-Me, 6-Br, etc.; R2 = C6H5, 4-MeC6H4, 4-FC6H4; R3 = C6H5, 4-MeC6H4, 3-FC6H4, etc.) and II with four consecutive stereocenters by simply changing the reaction solvents (THF or DCE). The Michael/aldol/retro-aldol/aldol sequential protocol allows the diastereodivergent synthesis of spirocyclopentaneoxindoles from 3-substituted oxindoles and α,β-unsaturated aldehydes under the relay catalysis of a chiral secondary amine and an NHC catalyst. Moreover, four stereoisomers of the product can be selectively provided by using different combinations of a chiral secondary amine and a solvent.

Chinese Chemical Letters published new progress about Aldol condensation. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Recommanded Product: 3-(4-Bromophenyl)acrylaldehyde.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Lu, Cong; Jing, Dong; Shen, Yanling; Luo, Jiajing; Zheng, Ke published the artcile< Redox-neutral access to 3,3'-disubstituted oxindoles via radical coupling reactions>, Recommanded Product: 3-Bromobenzotrifluoride, the main research area is arylpropanyl indolinone preparation; disubstituted oxindole redox active ester radical coupling.

In this paper, the results of using EDA complexes of in situ formed enolates with redox-active esters for radical-coupling reactions under mild conditions (metal-, photocatalyst-, and base-free) to afford (arylpropan-2-yl)indolin-2-ones I [R1 = H, Me, Boc; R2 = Me, Ph, 4-FC6H4, etc.; R3 = R4 = H, Me; R5 = Ph, 4-MeC6H4, 2-naphthyl, etc.] was reported. The leaving group from the substrate in these experiments was reused as a base in the reaction. This strategy could successfully be applied to a wide variety of primary, secondary, and tertiary alkyl radical precursors and oxindoles in radical-coupling reactions. The success of sunlight-driven transformation and gram-level synthesis via flow chem. delivered promising results for further application in industrial settings. Mechanistic investigation, including control experiments, and UV-vis spectroscopy provided insight into the mechanism.

Organic Chemistry Frontiers published new progress about Coupling reaction, homolytic. 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Recommanded Product: 3-Bromobenzotrifluoride.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sindelar, Karel; Jilek, Jiri O.; Pomykacek, Josef; Sedivy, Zdenek; Protiva, Miroslav published the artcile< Neurotropic and psychotropic agents. Part CXVIII. Synthesis of 2-acetyl and 3-acetyl derivatives of 8-chloro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin; 2-acyl-7-substituted thioxanthenes>, COA of Formula: C7H4BrNO4, the main research area is dibenzothiepin methylpiperazino; neurotropic methylpiperazinodibenzothiepin; psychotropic methylpiperazinodibenzothiepin; bactericide methylpiperazinodibenzothiepin; thioxanthene acyl; phenylthiophenylacetic acid cyclization; piperazinodibenzothiepin.

Reaction of 2-chlorodibenzo[b,f]thiepin with AcCl and AlCl3 proceeded under simultaneous acetylation of the nucleus and HCl addition with contraction of the central ring to give the thioxanthene I (R = Cl). Substitution reaction of I (R = Cl) with 1-methylpiperazine gave I (R = 4-methylpiperazino) and the elimination product II (X = CH2) was oxidized by air to II (X = O), also obtained by cyclization of 2-(4-acetylphenylthio)-5-chlorobenzoic acid. Total synthesis of the dibenzothiepins III (R1 = 2-, 3-MeCO; R2 = 4-methylpiperazino) were carried out. They started from the isomeric 2-(4-chlorophenylthio)-5(or4)-nitrobenzoic acids, the first of which was transformed in 6 steps to 5-amino-2-(4-chlorophenylthio)phenylacetic acid, which was cyclized to 2-amino-8-chlorodibenzo[b,f]thiepin-10(11H)-one. The 4-nitro acid, produced in 3 steps the homologous nitro acid, cyclized to 8-chloro-3-nitrodibenzo[b,f]thiepin-10(11H)-one. The Ac groups was introduced in III (R1 = 2-, 3-NH2; R2 = HO) by reaction of the diazonium salts with AcH semicarbazone followed by hydrolysis. The 2-acetyl- and 3-acetyl-8-chloro-10,11-dihydrodibenzo[b,f]thiepin-10-ol yielded by treatment with HCl 2-acetyl- and 3-acetyl-8,10-dichloro-10,11-dihydrodibenzo[b,f]thiepin, isomeric with I (R = Cl). Substitution reactions with 1-methylpiperazine gave III (R1 = 2-, 3-MeCO, R2 = 4-methylpiperazino) together with products of elimination, i.e. 2-acetyl- and 3-acetyl-8-chlorodibenzo[b,f]thiepin I (R = 4-methylpiperazino) when administered i.v. to mice, had a high central depressant activity, III (R1 = 2-MeCO, R2 = 4-methylpiperazino) had only mild activity; both substances in the test on rats were practically devoid of cataleptic activity (LD50 and ED50 given).

Collection of Czechoslovak Chemical Communications published new progress about Cyclocondensation reaction, intramolecular. 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, COA of Formula: C7H4BrNO4.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Qiu, Han-Yue; Fu, Jiang-Yan; Yang, Min-Kai; Han, Hong-Wei; Wang, Peng-Fei; Zhang, Ya-Han; Lin, Hong-Yan; Tang, Cheng-Yi; Qi, Jin-Liang; Yang, Rong-Wu; Wang, Xiao-Ming; Zhu, Hai-Liang; Yang, Yong-Hua published the artcile< Identification of new shikonin derivatives as STAT3 inhibitors>, Related Products of 14062-30-7, the main research area is shikonin derivative PMMB187 preparation antitumor breast STAT3 inhibitor; Anti-neoplastic; Breast cancer; Napabucasin (PubChem CID: 10331844); Plumbagin (PubChem CID: 10205); STA-21 (PubChem CID: 363709); STAT3 inhibitors; Shikonin; Shikonin (PubChem CID: 479503); Structural modifications.

The signal transducer and activator of transcription 3 is a constitutively activated oncogenic protein in various human tumors and represents a valid target for anticancer drug design. In this study, the authors have achieved a new type of STAT3 inhibitors based on structural modifications on shikonin scaffold, guided by computational modeling. By tests, PMMB-187 exhibited a more outstanding profile than shikonin on a small panel of human breast cancer cells, especially for the MDA-MB-231 cells. For the cellular mechanisms research, PMMB-187 was found to induce cell apoptosis in MDA-MB-231 cells, associated with the reduction of mitochondrial membrane potential, production of ROS and alteration of the levels of apoptosis-related proteins. Furthermore, PMMB-187 inhibited constitutive/inducible STAT3 activation, transcriptional activity, nuclear translocation and downstream target genes expression in STAT3-dependent breast cancer cells MDA-MB-231. Besides, no obvious inhibitory effect on activation of STAT1 and STAT5 was observed with PMMB-187 treatment. Most notably, the in vivo studies further revealed that PMMB-187 could dramatically suppress the MDA-MB-231 cells xenografted tumor growth. The in vitro and in vivo results collectively suggest that PMMB-187 may serve as a promising lead compound for the further development of potential therapeutic anti-neoplastic agents.

Biochemical Pharmacology (Amsterdam, Netherlands) published new progress about Antiproliferative agents. 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, Related Products of 14062-30-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nozawa-Kumada, Kanako; Ono, Kanako; Kurosu, Satoshi; Shigeno, Masanori; Kondo, Yoshinori published the artcile< Copper-catalyzed aerobic benzylic C(sp3)-H lactonization of 2-alkylbenzamides via N-centered radicals>, Application of C9H9BrO3, the main research area is methyl benzanilide oxygen copper catalyst lactonization reaction; isobenzofuranone preparation.

Copper-catalyzed aerobic C(sp3)-H functionalization of 2-alkylbenzamides for the synthesis of benzolactones were reported. This reaction proceeded via 1,5-hydrogen atom transfer of N-centered radicals directly generated by N-H bond cleavage and did not require the synthesis of pre-functionalized N-centered radical precursors or the use of strong stoichiometric oxidants.

Organic & Biomolecular Chemistry published new progress about Anilides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 17100-65-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H9BrO3, Application of C9H9BrO3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Brzeskiewicz, Jakub; Stanska, Barbara; Dabrowski, Piotr; Loska, Rafal published the artcile< C-H Activation and Cross-Coupling of Acyclic Aldonitrone>, Category: bromides-buliding-blocks, the main research area is ketonitrone preparation coupling acyclic aldonitrone heteroaryl bromide.

Palladium-catalyzed activation of C(sp2)-H bond in a readily E,Z-isomerizable aldonitrone, bearing an ester group at the C terminus, enabled its cross-coupling with a variety of aryl and heteroaryl bromides to give ketonitrones, including products with functional groups not compatible with the classical nitrone synthesis via condensation with hydroxylamines. The reactions proceeded with very high (usually complete) E selectivity. The key to obtaining good yields of the cross-coupling products was the use of sterically hindered carboxylic acid as additive and non-polar solvent (toluene), in which the starting nitrone exists mainly as E isomer. Further use of the obtained ketonitrones in dipolar cycloaddition or nucleophilic addition has also been demonstrated.

European Journal of Organic Chemistry published new progress about Alkoxycarbonyl groups. 5751-83-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H7BrO2S, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liu, Jian; Vasamsetty, Laxmaiah; Anwar, Muhammad; Yang, Shuang; Xu, Weici; Liu, Jinggong; Nagaraju, Sakkani; Fang, Xinqiang published the artcile< Organocatalyzed Kinetic Resolution of α-Functionalized Ketones: The Malonate Unit Leads the Way>, SDS of cas: 3893-18-3, the main research area is ketone kinetic resolution organocatalyst.

Developing a catalytic kinetic resolution (KR) protocol affording enantioenriched α-functionalized ketones (R/S)-RC(O)C(R1)(X)(CH2)nCH(C(O)OMe)2, (I) (R = Ph, ethoxy, benzyloxy, 2-furyl, etc.; R1 = Me, benzylthio, cyclohexylthio, etc.; n = 0, 1; X = H, D, F) with broad substrate scope and high efficiency has been a longstanding challenge. A successful protocol toward addressing this issue via an organocatalyzed cascade annulation was reported. The protocol could afford 11 classes of enantioenriched α-functionalized ketones (I) using a single catalytic system and avoid the frequent alterations of reaction conditions used in conventional methods. Up to 684 of the selectivity factor (s) is observed, and in most case, the s values are higher than 100. An aminolactam additive 1-(3-aminopropyl)azepan-2-one proves essential in promoting the resolution efficiency. Moreover, many previously unavailable enantiopure α-functionalized ketones are now accessible, and the annulation products are also useful building blocks and can be further transferred to densely substituted ketones without erosion of the optical purity. Mechanistically, in sharp contrast to the currently used direct one-step resolution patterns, a two-key-step resolution mode, in which the enantiomer discrimination happens at the second aldol step and the enantioenriched ketones are recovered by the reversible initial Michael reaction, is proposed, which provides opportunities addressing the challenging tasks that could not be solved by conventional resolution techniques.

ACS Catalysis published new progress about Aldol addition, stereoselective. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, SDS of cas: 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Goldberg, Frederick W.; Kettle, Jason G.; Xiong, Jian; Lin, Daoguang published the artcile< General synthetic strategies towards N-alkyl sulfoximine building blocks for medicinal chemistry and the use of dimethylsulfoximine as a versatile precursor>, COA of Formula: C7H4BrNO4, the main research area is alkyl sulfoximine preparation; sulfide amination oxidation alkylation.

The sulfoximine group has great potential as a substituent in drug discovery, as evidenced by two new clin. candidates, and can be viewed as an isosteric alternative to the commonly used sulfone. Our aim was to improve the accessibility of this group by synthesizing a diverse range of S-alkyl and N-alkyl sulfoximine building blocks with procedures that are applicable on a practical scale (>10 g). In particular, synthesis of the less well exploited N-alkyl sulfoximines and the use of dimethylsulfoximine as a versatile, com. available precursor is discussed.

Tetrahedron published new progress about Alkylation. 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, COA of Formula: C7H4BrNO4.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rabal, Obdulia; Sanchez-Arias, Juan A.; Cuadrado-Tejedor, Mar; de Miguel, Irene; Perez-Gonzalez, Marta; Garcia-Barroso, Carolina; Ugarte, Ana; Estella-Hermoso de Mendoza, Ander; Saez, Elena; Espelosin, Maria; Ursua, Susana; Tan, Haizhong; Wu, Wei; Xu, Musheng; Garcia-Osta, Ana; Oyarzabal, Julen published the artcile< Design, synthesis, biological evaluation and in vivo testing of dual phosphodiesterase 5 (PDE5) and histone deacetylase 6 (HDAC6)-selective inhibitors for the treatment of Alzheimer's disease>, Quality Control of 85070-57-1, the main research area is phosphodiesterase PDE5 histone deacetylase HDAC6 inhibitor Alzheimer disease; Alzheimer; Dual inhibitors; HDAC6 selective; In-vivo test; PDE5 inhibition; Pharmacological tool compound; Tg2576 mice.

The authors have identified chem. probes that act as dual phosphodiesterase 5 (PDE5) and histone deacetylase 6 (HDAC6)-selective inhibitors (>1 log unit difference vs. class I HDACs) to decipher the contribution of HDAC isoforms to the pos. impact of dual-acting PDE5 and HDAC inhibitors on mouse models of Alzheimer’s disease (AD) and fine-tune this systems therapeutics approach. Structure- and knowledge-based approaches led to the design of first-in-class mols. with the desired target compound profile: dual PDE5 and HDAC6-selective inhibitors. Compound 44b (5-[[4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl]methyl]thiophene-2-carbohydroxamic acid), which fulfilled the biochem., functional and ADME-Tox profiling requirements and exhibited adequate pharmacokinetic properties, was selected as pharmacol. tool compound and tested in a mouse model of AD (Tg2576) in vivo.

European Journal of Medicinal Chemistry published new progress about Alzheimer disease. 85070-57-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8BrFO2, Quality Control of 85070-57-1.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tuccinardi, Tiziano; Bertini, Simone; Martinelli, Adriano; Minutolo, Filippo; Ortore, Gabriella; Placanica, Giorgio; Prota, Giovanni; Rapposelli, Simona; Carlson, Kathryn E.; Katzenellenbogen, John A.; Macchia, Marco published the artcile< Synthesis of Anthranylaldoxime Derivatives as Estrogen Receptor Ligands and Computational Prediction of Binding Modes>, Reference of 19128-48-4, the main research area is anthranyl aldoxime preparation estrogen receptor ligand.

N-Me-anthranylaldoximes possess a hydrogen-bonded pseudocyclic A’ ring in place of the typical phenolic A-ring that is characteristic of most estrogen receptor (ER) ligands. We have investigated the role played by substituents introduced into either one or both of the peripheral 3- and 4-Ph rings in modulating ER binding affinity. An efficient synthetic strategy was employed for the preparation of differentially substituted 3- and 4-aryl derivatives that involved exploiting the different reactivity of bromo- vs. chloro-aryl groups in palladium-catalyzed cross-couplings. The binding data showed that ERα affinity could be improved by a single p-OH group in the 4-Ph ring, whereas the same substitution on the 3-Ph ring caused a dramatic reduction of ERβ affinity. The most ERα-selective compound was the one with two p-OH groups on both Ph substituents. To rationalize these results, ligand docking followed by mol. mechanics Poisson-Boltzmann/surface area (MM-PBSA) studies were carried out. These analyses suggested a mol. basis for the interaction of these compounds with the ERs and enabled the development of models able to predict the mode of ligand binding.

Journal of Medicinal Chemistry published new progress about Estrogen receptor α Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 19128-48-4 belongs to class bromides-buliding-blocks, and the molecular formula is C6H3BrClNO2, Reference of 19128-48-4.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary