Tag: M.W=200-250

Parhi, Biswajit; Gurjar, Jitendra; Pramanik, Suman; Midya, Abhisek; Ghorai, Prasanta published the artcile< Organocatalytic Enantioselective Intramolecular Oxa-Michael Reaction of Enols: Synthesis of Chiral Isochromenes>, Computed Properties of 89003-95-2, the main research area is isochromene enantioselective synthesis; oxa Michael reaction enol squaramide catalyst.

An unprecedented enantioselective intramol. oxa-Michael reaction of enols has been described. A squaramide-containing tertiary amine based bifunctional organocatalyst efficiently activates the o-homoformyl chalcones to provide the chiral isochromenes in moderate yields and good to excellent enantioselectivities. Further, late-stage functionalizations of the vinyl ether moiety of the chiral isochromene products have also been exemplified.

Journal of Organic Chemistry published new progress about Benzopyrans Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 89003-95-2 belongs to class bromides-buliding-blocks, and the molecular formula is C8H4BrNO, Computed Properties of 89003-95-2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Kurppa, Kari J.; Liu, Yao; To, Ciric; Zhang, Tinghu; Fan, Mengyang; Vajdi, Amir; Knelson, Erik H.; Xie, Yingtian; Lim, Klothilda; Cejas, Paloma; Portell, Andrew; Lizotte, Patrick H.; Ficarro, Scott B.; Li, Shuai; Chen, Ting; Haikala, Heidi M.; Wang, Haiyun; Bahcall, Magda; Gao, Yang; Shalhout, Sophia; Boettcher, Steffen; Shin, Bo Hee; Thai, Tran; Wilkens, Margaret K.; Tillgren, Michelle L.; Mushajiang, Mierzhati; Xu, Man; Choi, Jihyun; Bertram, Arrien A.; Ebert, Benjamin L.; Beroukhim, Rameen; Bandopadhayay, Pratiti; Awad, Mark M.; Gokhale, Prafulla C.; Kirschmeier, Paul T.; Marto, Jarrod A.; Camargo, Fernando D.; Haq, Rizwan; Paweletz, Cloud P.; Wong, Kwok-Kin; Barbie, David A.; Long, Henry W.; Gray, Nathanael S.; Janne, Pasi A. published the artcile< Treatment-Induced Tumor Dormancy through YAP-Mediated Transcriptional Reprogramming of the Apoptotic Pathway>, Recommanded Product: 3-Bromobenzotrifluoride, the main research area is tumor dormancy YAP transcriptional reprogramming apoptotic pathway; YAP; dormancy; drug resistance; drug tolerance; epidermal growth factor receptor; lung cancer; senescence.

Eradicating tumor dormancy that develops following epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor (TKI) treatment of EGFR-mutant non-small cell lung cancer, is an attractive therapeutic strategy but the mechanisms governing this process are poorly understood. Blockade of ERK1/2 reactivation following EGFR TKI treatment by combined EGFR/MEK inhibition uncovers cells that survive by entering a senescence-like dormant state characterized by high YAP/TEAD activity. YAP/TEAD engage the epithelial-to-mesenchymal transition transcription factor SLUG to directly repress pro-apoptotic BMF, limiting drug-induced apoptosis. Pharmacol. co-inhibition of YAP and TEAD, or genetic deletion of YAP1, all deplete dormant cells by enhancing EGFR/MEK inhibition-induced apoptosis. Enhancing the initial efficacy of targeted therapies could ultimately lead to prolonged treatment responses in cancer patients.

Cancer Cell published new progress about Aging, animal. 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Recommanded Product: 3-Bromobenzotrifluoride.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Dewar, Michael J. S.; Poesche, Werner H. published the artcile< New heteroaromatic compounds. XVIII. Boron-containing analogs of benz[a]anthracene>, Name: 4-Bromoisobenzofuran-1,3-dione, the main research area is .

The amines, 2,3-Ph(H2N)C10H6 (I) and 2-(2-H2NC6H4)C10H7 (II) on treatment with BCl3 and a catalytic amount of AlCl3 in boiling xylene gave the corresponding chloroborazarobenz[a]anthracenes (III, R = Cl) (IV) and (V, R = Cl) (VI). NaNO2 (55 ml., 2M) in concentrated H2SO4 stirred below 25° with addition of 18.8 g. 3,2-O2N(H2N)C10H6 in 670 ml. AcOH (boiled and cooled rapidly to 20°) and the mixture kept 15 min., added with stirring to 38 g. CuBr in 200 ml. 48% HBr and kept overnight, and diluted with H2O yielded 54% 3,2-Br(O2N)C10H6, m. 79-80°. The compound (20.8 g.) and 55 g. PhI stirred 36 hrs. at 110° with 31.8 g. Cu bronze yielded 74% 3,2-Ph(O2N)C10H6 (VII), m. 96.0-6.8° (MeOH). VII (6.0 g.) and 0.2 g. 10% Pd-C in 230 ml. boiling alc. treated gradually with 20 ml. N2H4.H2O and kept 1 hr. yielded quant. I, m. 82.7-3.5° (90% MeOH). I (10 g.) in 160 ml. dry xylene added (N atm.) slowly to 7.0 g. BCl3 in 45 ml. ice-cold xylene and the mixture treated with 0.2 g. AlCl3, the mixture heated to 140° in 4 hrs. and the temperature maintained 16 hrs., cooled and taken up in 750 ml. 2:1 Et2O-C6H6, the H2O-washed and dried (MgSO4) solution evaporated on a steam bath and the residue taken up in 500 ml. hot MeOH, the solution concentrated and kept at -15°, the product recovered from hot MeOH and the purified material (4.2 g.) recrystallized using an efficient dry box gave III (R = OMe) (VIII), m. 159° (evacuated capillary). The mother liquors gave 0.85 g. III (R = 1/2 O), C32H22B2N2O, m. 322°. VIII (1.3 g.) in 40 ml. dry Et2O stirred (H2O-free atm.) at 0° with addition of 12.5 ml. 0.6M MeMgBr and the mixture stirred 24 hrs. with rise of temperature to 20, the filtered solution evaporated and the residue sublimed at 150°/0.005 mm. gave III (R = Me) (VIIIa), m. 160.0-1.3° (petr. ether, b. 60-8°). LiAlH4 (1.35 millimoles) added to 3.86 millimoles VIII in 40 ml. dry Et2O and the mixture refluxed 2 hrs. with 0.45 millimole AlCl3 gave 5,6-borazarobenz[a]anthracene (III, R = H) (IX), m. 139° (decomposition). Cu bronze (46.5 g.), 65.0 g. 2-IC10H7, and 56.0 g. 1,2-Br(O2N)C6H4 stirred 40 hrs. at 110° gave 60% 2-(o-O2NC6H4)C10H7 (X), m. 101° (MeOH). X (9.0 g.) in 450 ml. alc. hydrogenated at 20° and 30 lb./in.2 with 0.3 g. 10% Pd-C and the filtered solution concentrated gave 6.0g. II, m. 95-7°. X (32 g.) and 1.0 g. 10% Pd-C refluxed 1 hr. in 1400 ml. alc. with gradual addition of 45 ml. N2H4.H2C and the filtered solution concentrated gave 22 g. II. II (22.0 g.) in 350 ml. dry xylene added slowly with stirring to 13.0 g. BCl3 in 100 ml. ice-cold xylene and the mixture heated 4 hrs. at 140° with 0.5 g. AlCl3 and stirred 16 hrs. at 140° gave 10.4 g. V (R = 1/2 O) (XI), m. 261-4°, recrystallized from PhMe(C) to give an analytical sample, m. 275.5°. Further concentration of the mother liquors gave a 2nd crop of XI (4.8 g., m. 264-5°), and evaporation of the filtrate yielded 8.6 g. residue (XII), m. 225-47°. The ether XI (12.7 g.) taken up in 500 ml. hot absolute MeOH and concentrated to 350 ml., cooled and the product (10.5 g., m. 174-6°) recrystallized from MeOH (C) gave V (R = OMe) (XIII), m. 183-4° (evacuated capillary). The filtrate evaporated and the residue combined with XII, the mixture recrystallized from absolute MeOH to give 4.80 g. XIII, and the filtrate evaporated in vacuo gave a dark brown oil with an ultraviolet spectrum identical with that of XIII and containing no other bands. XIII (2.6 g.) stirred at 20° in 100 ml. dry Et2O with dropwise addition of 15 ml. M MeMgBr in Et2O and the mixture stirred 2 hrs., the filtered solution diluted with moist Et2O and shaken with H2O, the organic layer dried over CaCl2 and evaporated yielded 87% product, m. 136-40°, sublimed at 120°/0.1 mm. to give V (R = Me) (XIV), m. 141-3°. XIII (1.00 g.) stirred at 0° in 30 ml. dry Et2O with gradual addition of 1.00 millimole LiAlH4 (standardized Et2O solution) and the mixture refluxed 2 hrs. with 0.04 g. AlCl3, the filtered solution evaporated and the residue sublimed at 120°/0.005 mm. gave 65% V (R = H) (XV), m. 136.5-7.0° (decomposition). XIII (2.0 g.) in 20 ml. hot AcOH treated with 10 ml. concentrated HCl and the mixture cooled quickly to 5°, diazotized with 0.60 g. NaNO2 in a min. of H2O and kept 2 hrs., added with stirring to 300 ml. boiling H2O and the mixture boiled 30 min., kept overnight and the precipitate recrystallized twice from PhMe(C) gave 64% 6-hydroxy-6,5-boroxarobenz[a]-anthracene (XVI), m. 279.5-81.0°. The cyclization of II to V rather than to a borazachrysene illustrated very clearly the large steric requirements of the Friedel-Crafts reaction. The charge transfer spectra of the complexes formed by III and V with tetracyanoethylene (XVII) were determined in CHCl3. No difficulty was encountered with the Me or MeO derivatives, VIII, VIIIa, XIII, or XIV, all of which gave stable colorations with XVII, but the parent compounds, IX and XV, reacted rapidly with the acceptor. XV in CHCl3 and XVII in CHCl3 initially gave a green mixture rapidly changing to violet before fading and forming a white precipitate The ultraviolet spectrum of the final colorless solution was identical with that of XIII, suggesting that EtOH in the CHCl3 was forming V (R = OEt) and precipitating (NC)2CHCH(CN)2. The wave lengths of the charge transfer spectra of XVII complexes are given (compound and wave lengths of charge transfer band in A given): IX, 614; VIII, 627; VIIIa, 620; XV, 690, 477; XIII, 701, 500; XIV, 704, 486. The π-electron distribution in these compounds is probably too uneven for first-order perturbation theory to be applicable. The ultra violet spectra of IX and XV in methylcyclohexane and alc.-free CHCl3, and of VIII, XIII, VIIIa, and XIV in CHCl3 were tabulated with the spectrum of benz[a]anthracene (XVIII) in methylcyclohexane listed for comparison. The estimated band maximum (mμ of π-π transitions in methyl cyclohexane for XVIII, IX, and XV were tabulated. The spectra of IX and XV are very similar to that of XVIII, the main difference being an increase in intensity of the α-bands in the hetero aromatics, in accordance with theory.

Journal of the American Chemical Society published new progress about Entropy. 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, Name: 4-Bromoisobenzofuran-1,3-dione.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sander, Kerstin; Galante, Eva; Gendron, Thibault; Yiannaki, Elena; Patel, Niral; Kalber, Tammy L.; Badar, Adam; Robson, Mathew; Johnson, Sean P.; Bauer, Florian; Mairinger, Severin; Stanek, Johann; Wanek, Thomas; Kuntner, Claudia; Kottke, Tim; Weizel, Lilia; Dickens, David; Erlandsson, Kjell; Hutton, Brian F.; Lythgoe, Mark F.; Stark, Holger; Langer, Oliver; Koepp, Matthias; Arstad, Erik published the artcile< Development of Fluorine-18 Labeled Metabolically Activated Tracers for Imaging of Drug Efflux Transporters with Positron Emission Tomography>, SDS of cas: 128577-47-9, the main research area is fluorine 18 PET tracer imaging drug efflux transporter.

Increased activity of efflux transporters, e.g., P-glycoprotein (P-gp) and breast cancer resistance protein (BCRP), at the blood-brain barrier is a pathol. hallmark of many neurol. diseases, and the resulting multiple drug resistance represents a major clin. challenge. Noninvasive imaging of transporter activity can help to clarify the underlying mechanisms of drug resistance and facilitate diagnosis, patient stratification, and treatment monitoring. We have developed a metabolically activated radiotracer for functional imaging of P-gp/BCRP activity with positron emission tomog. (PET). In preclin. studies, the tracer showed excellent initial brain uptake and clean conversion to the desired metabolite, although at a sluggish rate. Blocking with P-gp/BCRP modulators led to increased levels of brain radioactivity; however, dynamic PET did not show differential clearance rates between treatment and control groups. Our results provide proof-of-concept for development of prodrug tracers for imaging of P-gp/BCRP function in vivo but also highlight some challenges associated with this strategy.

Journal of Medicinal Chemistry published new progress about ATP-binding cassette transporter ABCG2 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 128577-47-9 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8BrFO2, SDS of cas: 128577-47-9.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Jia, Min-Qiang; Li, Guo-Tai; You, Shu-Li published the artcile< DPEN-derived triazolium salts catalyzed annulation reactions of α,β-unsaturated aldehydes with 1,3-dicarbonyl compounds>, Application of C9H7BrO, the main research area is unsaturated aldehyde dicarbonyl enantioselective annulation triazolium catalyst mol sieves; hydropyrone asym synthesis.

Enantioselective N-heterocyclic carbene-catalyzed annulation reactions of α,β-unsaturated aldehydes with various dicarbonyl compounds were carried out. With 10 mol% of a (1R,2R)-1,2-diphenylethylamine- (DPEN)-derived triazolium salt, 15 mol% of DBU, 4 Å mol. sieves, and 100 mol% of quinone as the oxidant, various 3,4-dihydro-α-pyrones were obtained in good yields and enantioselectivity (≤92% yield, 88% ee).

International Journal of Chemistry (Mumbai, India) published new progress about 1,3-Dicarbonyl compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Application of C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wang, Zhan-Yong; Yang, Ting; Wang, Kai-Kai; Chen, Rongxiang; Liu, Menghan; Liu, Hongxin published the artcile< Oxidative N-heterocyclic carbene-catalyzed [3 + 3] annulation reaction of enals with benzofuran-3-ones: efficient access to benzofuran-fused δ-lactones>, COA of Formula: C9H7BrO, the main research area is benzofuranone enal azacyclic carbene catalyst heterocyclization; dihydropyranobenzofuranone preparation.

A facile route to benzofuran-fused δ-lactones was developed via an N-heterocyclic carbene-catalyzed [3 + 3] annulation reaction, giving the expected products in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee). It should be noted that benzofuran-fused pyrones can be obtained stepwise in one pot with excellent yields (up to 96%) by using this methodol.

Organic Chemistry Frontiers published new progress about Benzofurans Role: RCT (Reactant), RACT (Reactant or Reagent). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, COA of Formula: C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Stoicescu-Crivetz, L.; Mandasescu, L. published the artcile< The antituberculotic action of some hydrazide and hydrazone derivatives of the p-amino-o-halobenzoic acids>, Category: bromides-buliding-blocks, the main research area is .

The following derivatives of the p-amino-o-halobenzoic acids were prepared to test the hydrazides and hydrazones for their tuberculostatic activity. The Me ester (I) of 2,4-Cl(O2N)C6H3CO2H (II) (6 g.), obtained by slowly adding 8 mL. concentrated H2SO4 to a solution of 6 g. II in 160 mL. MeOH and heating 6-8 h., m. 78-80° (from dilute EtOH). The analogous Br (III), m. 84°, and the iodo, m. 88°, compounds were prepared in the same way. 2,4-Cl(H2N)C6H3CO2Me, obtained by reduction of I with SnCl2 and HCl, m. 104° (from H2O). The Br, m. 94°, and iodo, m. 120°, analogs were obtained similarly. The hydrazide (1.5 g.) of 2,4-Cl(H2N)C6H3CO2H, prepared by adding dropwise 3 g. N2H4.H2O to 3 g. I, m. 175° (from dilute EtOH). The Br analog was obtained by the same method from III. 4-Amino-2-chlorobenzoylhydrazones of the following aldehydes were prepared: o-HOC6H4CHO, m. 190°; BzH, m. 195°; m-HOC6H4CHO, m. 226°; p-Me2NC6H4CHO; p-AcNHC6H4CHO, m. 255°. 4-Amino-2-bromobenzoylhydrazones: o-HOC6H4CHO, m. 215°; m-HOC6H4CHO, m. 226°; p-Me2NC6H4CHO, m. 207°. The hydrazides and hydrazones had a very weak antituberculotic action.

Studii si Cercetari de Chimie published new progress about Catalysts. 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Xia, Ai-Bao; Pan, Gong-Jian; Wu, Chao; Liu, Xue-Li; Zhang, Xiao-Long; Li, Zhao-Bo; Du, Xiao-Hua; Xu, Dan-Qian published the artcile< Enantioselective One-Pot Reaction: Organocatalyzed Synthesis of Fully Functionalized Oxabicyclo[2.2.2]octanes with Seven Contiguous Stereocenters>, Product Details of C9H7BrO, the main research area is stereoselective preparation oxabicyclooctane seven contiguous stereocenter; organocatalytic stereoselective Michael Henry hemiacetalization unsaturated aldehyde ketoamide nitroalkene.

An enantioselective one-pot Michael/ Michael/ Henry/ hemiacetalization reaction between α,β-unsaturated aldehydes, α-ketoamides, and nitroalkenes under mild conditions catalyzed by a diarylprolinol silyl ether has been developed. The sequential methodol. provides a direct approach to a wide range of fully substituted chiral oxabicyclo[2.2.2]octanes with seven contiguous stereocenters in moderate to excellent yields (up to 99%), high to excellent diastereoselectivities (up to >25:1 dr), and high to excellent enantioselectivities (up to 99% ee).

Advanced Synthesis & Catalysis published new progress about Acetalization. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Product Details of C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Jin, Zhichao; Huang, Huicai; Li, Wenjun; Luo, Xiaoyan; Liang, Xinmiao; Ye, Jinxing published the artcile< Enantioselective Organocatalytic Synthesis of Oxazolidine Derivatives through a One-Pot Cascade Reaction>, Application In Synthesis of 3893-18-3, the main research area is aryl amide unsaturated aldehyde enantioselective organocatalytic cascade reaction; oxazolidine stereoselective preparation.

An asym. organocatalytic cascade reaction of aryl amides, e.g., I, and α,β-unsaturated aldehydes which can afford a series of oxazolidine derivatives, e.g., II, has been developed. The one-pot reaction reported here can produce an oxazolidine derivative in a highly enantioselective manner and good yield with good to excellent diastereomeric ratio.

Advanced Synthesis & Catalysis published new progress about Aromatic amides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Application In Synthesis of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Yin, Biaolin; Cai, Congbi; Zeng, Guohui; Zhang, Ruoqi; Li, Xiang; Jiang, Huanfeng published the artcile< A Novel Entry to Functionalized Benzofurans and Indoles via Palladium(0)-Catalyzed Arylative Dearomatization of Furans>, Computed Properties of 81107-97-3, the main research area is benzofuran indole preparation palladium phosphine catalyst furan ring opening; furan arylation dearomatizatin palladium phosphine catalyst benzofuran indole preparation.

A novel entry to functionalized benzofurans and indoles from furans in moderate to good yields has been developed. This protocol involves palladium(0)-catalyzed dearomatizing intramol. arylation of the furan ring, formation of a π-allylic palladium complex, furan ring opening, and a β-hydride elimination sequence.

Organic Letters published new progress about Arylation (intramol.). 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