Tag: M.W=200-250

Yee, Ying K.; Bernstein, Peter R.; Adams, Edward J.; Brown, Frederick J.; Cronk, Laura A.; Hebbel, Kevin C.; Vacek, Edward P.; Krell, Robert D.; Snyder, David W. published the artcile< A novel series of selective leukotriene antagonists: exploration and optimization of the acidic region in 1,6-disubstituted indoles and indazoles>, Name: Methyl 4-(bromomethyl)-3-fluorobenzoate, the main research area is leukotriene antagonistic MSBAR indole indazole preparation; antiasthmatic indole indazole preparation.

A systematic structure-activity exploration of the carboxylic acid region in a series of indole- or indazole-derived leukotriene antagonists I [e.g., R = Me(CH2)3CHEt, X = CH, N, R1 = CO2H] led to several discoveries. Use of the 3-methoxy-p-tolyl fragment (illustrated in I) for connecting the indole and the acidic site provides the most potent carboxylic acids I (R = CO2H) tetrazoles I (R1 = tetraacyl) and aryl sulfonimides, e.g I (R = PhSO2NHCO). The aryl sulfonimides are 5-500 times more potent (in vitro and/or in vivo) than the corresponding carboxylic acids. The o-tolyl sulfonimides such as I (R = cyclohexylmethyl, X = N, R1 = 2-MeC6H4SO2NHCO) show greater oral potency than the Ph sulfonimides at a given level of in vitro activity. Acidic sulfone derivatives e.g., I [R = cyclopentylmethyl; X = CH, N; R1 = PhSO2CH(CO2Me)]-(Nu = CH(CO2CH3)SO2Ph) mimic the activity of the acidic imides.

Journal of Medicinal Chemistry published new progress about Antiasthmatics. 128577-47-9 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8BrFO2, Name: Methyl 4-(bromomethyl)-3-fluorobenzoate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Meng, He; Bai, Shiming; Qiao, Yu; He, Ting; Li, Weiyi; Ming, Jialin published the artcile< Rhodium-Catalyzed Three-Component Reaction of Alkynes, Arylzinc Chlorides, and Iodomethanes Producing Trisubstituted/Tetrasubstituted Alkenes with/without 1,4-Migration>, Safety of 3-Bromobenzotrifluoride, the main research area is alkene diastereoselective preparation; alkyne arylzinc chloride iodomethane rhodium catalyst three component.

A three-component reaction of alkynes, arylzinc chlorides and iodomethanes was found to proceed in the presence of a rhodium catalyst to give high yields of trisubstituted/tetrasubstituted alkenes I [R = 2-MeC6H4, 2-Me-4-MeOC6H3, 2-furyl, etc.; R1 = H, Me; R2 = Me, n-Pr, (CH2)4I, etc.; R3 = Me, n-Pr, (CH2)3OMe, etc.; R2R3 = (CH2)10]. The usual arylzinc chlorides only gave trisubstituted alkenes, generated through a migratory carbozincation-cross-coupling sequence, where 1,4-Rh migration from an alkenyl carbon to an aryl carbon occurred. In contrast, 5-membered heteroarylzinc chlorides only gave the tetrasubstituted alkenes via a carborhodation-cross-coupling pathway without 1,4-migration.

Organic Letters published new progress about Alkenes Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Safety of 3-Bromobenzotrifluoride.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Achard, Thierry; Belokon’, Yuri N.; Fuentes, Jose A.; North, Michael; Parsons, Teresa published the artcile< Influence of aromatic substituents on metal(II)salen catalyzed, asymmetric synthesis of α-methyl α-amino acids>, Electric Literature of 81107-97-3, the main research area is amino acid methyl asym synthesis; alanine derivative asym benzylation salen copper catalyst mol structure; transition metal Schiff base complex catalyst preparation mol structure.

The influence of substituents on both the aromatic rings of the catalyst, and the benzylidene unit of the substrate are investigated in the (salen)copper(II) catalyzed asym. benzylation of alanine derivatives Catalysts with electron-donating, and electron-withdrawing substituents of various sizes and at various locations on the aromatic rings of the salen ligand were prepared, but all exhibited inferior enantioselectivity to the parent (salen)copper(II) complex. In contrast, the introduction of halogenated substituents onto the aromatic ring of the N-benzylidene alanine Me ester substrate was found to enhance the enantioselectivity of the alkylation with a para-chloro substituent giving optimal results. A new procedure for the preparation of the catalysts which avoids the need for chromatog. on sephadex LH20 is reported, and the optimal catalyst obtained in this way was found to be a cobalt(salen) complex.

Tetrahedron published new progress about Amino acids Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 81107-97-3 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3O, Electric Literature of 81107-97-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Bolchi, Cristiano; Pallavicini, Marco; Rusconi, Chiara; Diomede, Luisa; Ferri, Nicola; Corsini, Alberto; Fumagalli, Laura; Pedretti, Alessandro; Vistoli, Giulio; Valoti, Ermanno published the artcile< Peptidomimetic inhibitors of farnesyltransferase with high in vitro activity and significant cellular potency>, Safety of 2-Bromo-4-nitrobenzoic acid, the main research area is peptidomimetic inhibitor farnesyltransferase antiproliferative aorta smooth muscle atherosclerosis.

2-O-Tolyl or 2-o-anisyl substituted 4-hydroxy- and 4-carboxybenzamides of methionine, etherified and amidified with 2-hydroxymethyl- and 2-aminomethylpyridodioxane, resp., are described as inhibitors of Ras protein farnesyltransferase (FTase). Of the sixteen compounds, resulting from the substitution pattern of benzamide and the configuration of the two stereocenters, seven inhibited FTase activity with potencies in the nanomolar range. They were all 2-oxymethylpyridodioxane ethers and, among them, the four o-tolyl substituted stereoisomers also showed micromolar antiproliferative effect on human aortic smooth muscle cells interfering with Ras farnesylation. The docking anal. enlightened significant differences in enzyme interaction between oxymethylpyridodioxane and aminomethylpyridodioxane derivatives

Bioorganic & Medicinal Chemistry Letters published new progress about Antiatherosclerotics. 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, Safety of 2-Bromo-4-nitrobenzoic acid.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wu, Ping; Zhang, Xueguo; Chen, Baohua published the artcile< Direct synthesis of 2,4,5-trisubstituted imidazoles and di/tri-substituted pyrimidines via cycloadditions of α,β-unsaturated ketones/aldehydes and N'-hydroxyl imidamides>, Application of C9H7BrO, the main research area is hydroxyamidine phenyl arylpropenone iron catalyst iodine promoter cycloaddition; aroyl phenylimidazole regioselective preparation green chem; unsaturated carbonyl compound hydroxyamidine iron catalyst cycloaddition green chem; diarylpyrimidine regioselective preparation.

An efficient route for the synthesis of 5-acetylimidazoles and di/trisubstituted pyrimidines via iron-catalyzed cross-dehydrogenative coupling (CDC), with excellent tolerance and yields was developed. α,β-Unsaturated aldehydes/ketones and N’-hydroxyl imidamides underwent [3+2] and [3+3] cycloadditions in two processes, involving iron-mediated Michael reaction, Robinson Annulation and 1,5-electrocyclization.

Tetrahedron Letters published new progress about [3+2] Cycloaddition reaction (regioselective). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Application of C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Schmidt, Michael A. published the artcile< Effect of Terminal Alkylation of Aryl and Heteroaryl Hydrazines in the Fischer Indole Synthesis>, Recommanded Product: Ethyl 5-bromothiophene-2-carboxylate, the main research area is Fischer indole synthesis; hydrazine ketone alkylation amidation cross coupling.

The effect of alkylation on the terminal position of aryl and heteroaryl hydrazines in the Fischer indole synthesis was examined Compared to their unalkylated counterparts, reactions using alkylated s provided indole products with higher yields and faster rates. The reactions can be conducted at lower temperatures and are compatible with acid-sensitive functionality. The terminally alkylated hydrazines were readily prepared by a new two-step sequence and held as stable hydrazinium salts. The mild formation of the salts along with the favorable Fischer indole reaction conditions highlights the potential of this approach in later-stage synthetic use.

Journal of Organic Chemistry published new progress about Alkylation. 5751-83-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H7BrO2S, Recommanded Product: Ethyl 5-bromothiophene-2-carboxylate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ikeuchi, Yutaka; Taguchi, Takeo; Hanzawa, Yuji published the artcile< Zirconocene-Mediated and/or Catalyzed Unprecedented Coupling Reactions of Alkoxymethyl-Substituted Styrene Derivatives>, Safety of Methyl 2-bromo-5-fluorobenzoate, the main research area is alkoxymethylstyrene alkoxy cleavage regioselective stereoselective homodimerization heterodimerization; hydrochrysene stereoselective preparation; aryl hydronaphthalene stereoselective preparation; zirconocene mediated stereoselective cyclization dimerization coupling ortho alkoxymethyl styrene; dependence product zirconocene mediated reaction alkoxymethyl styrene.

2-(Alkoxymethyl)styrenes I (R = H, Me; R1 = H, F, MeO; R2 = Me, PhCH2) undergo a variety of reactions involving cleavage of the alkoxy group with zirconocene generated from zirconocene dichloride and either butyllithium or butylmagnesium chloride. I (R = H) react with stoichiometric amounts of zirconocene to give 4-substituted-2-methylstyrenes or 4-substituted-2-(deuteromethyl)styrenes, while with two equivalent of zirconocene, I (R = R1 = H; R2 = PhCH2) gives 3-ethyl-1-(2-methylphenyl)butane or a trideuterated derivative; in the presence of catalytic zirconocene and 3 equivalent of butylmagnesium chloride, I (R = H; R1 = H, F; R2 = PhCH2) give mainly hexahydrochrysenes II (R = H; R1 = H, F) in 52-57% yields. In the presence of either catalytic or stoichiometric amounts of zirconocene, I (R = Me; R1 = H, F, MeO; R2 = Me, PhCH2) give II (R = Me; R1 = H, F, MeO) in 29-89% yields; with I (R = Me; R1 = F; R2 = Me), the aryltetrahydronaphthalene III {R1 = F; R3 = 2-[(MeO)Me2C]C6H4} is obtained in the presence of stoichiometric zirconocene in 28-50% yields as a single stereoisomer. I (R = Me; R1 = H; R2 = Me) couples with excess amounts of arylethylenes R3CH:CH2 [R3 = Ph, 4-FC6H4, 3,5-(F3C)2C6H3, 4-MeOC6H4, 2-MeOC6H4] in the presence of stoichiometric zirconocene to yield aryldihydronaphthalenes III [R1 = H; R3 = Ph, 4-FC6H4, 3,5-(F3C)2C6H3, 4-MeOC6H4, 2-MeOC6H4] in 11-85% yields (as single stereoisomers) in addition to 5-60% yields of II (R = Me; R1 = H).

Journal of Organic Chemistry published new progress about Aryl alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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

Thanikachalam, Venugopal; Jayabharathi, Jayaraman; Karunakaran, Uthirapathy; Anudeebhana, Jagathratchagan; Thilagavathy, Shanmugam; Sivaraj, Seker published the artcile< Angular shaped AIE generator based luminophores for mechanochromism: An explosive sensor>, Reference of 3893-18-3, the main research area is aggregation induced emission enhancement generator based luminophore mechanochromism.

We have synthesized (E)-N,N-diphenyl-4-(2-(2-(4′-(1,2,2-triphenylvinyl)-[1,1′-biphenyl]- 4-yl)vinyl)- 1H-phenanthro[9,10-d]imidazol-1-yl)aniline (TPE-DBPPI) and (E)- 2-(4′-(2-(1-(4-(diphenylamino)phenyl)- 1H-phenanthro[9,10-d]imidazol-2-yl)vinyl)-[1,1′-biphenyl]- 4-yl)- 3,3-diphenylacrylonitrile (TPA-PPICN) consist of triphenylamine (donor), phenanthroimidazole (acceptor) and tetraphenylethylene (AIE generator). The twisted TPE-DBPPI and TPA-PPICN depict aggregation induced emission enhancement (AIEE) and demonstrated mechanochromic (MC) behavior between blue and green emission. The restricted-intramol.-rotation (RIR) of aryl rings of TPE (TPE-DBPPI) and TPA (TPA-PPICN) in the aggregated phase reduced the non-radiative relaxation channel hence, increase of emission intensity with high photoluminescence quantum yield (PLQY) in film state was observed The PLQY of TPE-DBPPI / TPA-PPICN in various phases are of 58/76% (pristine), 62/83% (grinding) and 65/88% (annealing). The film optical studies and powder XRD (PXRD) analyses implies that the change of twisted crystalline phase of TPE-DBPPI and TPA-PPICN to planar amorphous state results in mechanochromism. Also, these materials detect picric acid in aqueous and film owing to the proton-binding ability of azomethine nitrogen of imidazole which was confirmed by both NMR and DFT studies. The high neg. ΔGet [- 3.01 eV (TPE-DBPPI) and – 3.06 eV (TPA-PPICN)] indicates the thermodn. feasibility of photo electron transfer (PET) process.

Materials Today Communications published new progress about Absorption. 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

Sun, Wangsheng; Zhu, Gongming; Hong, Liang; Wang, Rui published the artcile< The Marriage of Organocatalysis with Metal Catalysis: Access to Multisubstituted Chiral 2,5-Dihydropyrroles by Cascade Iminium/Enamine-Metal Cooperative Catalysis [Erratum to document cited in CA156:362840]>, Product Details of C9H7BrO, the main research area is erratum enantioselective aza Michael carbocyclization reaction unsaturated aldehyde tosylpropargylamine; organo metal cooperative catalyst enantioselective synthesis erratum; pyrrole aryl dihydro enantioselective synthesis erratum.

On page 13962, Reference 14 contained an incorrect CCDC number; the corrected number is given.

Chemistry – A European Journal published new progress about Amines, propargyl Role: RCT (Reactant), RACT (Reactant or Reagent). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Product Details of C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

De la Mare, P. B. D.; Harvey, J. T. published the artcile< Kinetics and mechanisms of aromatic halogen substitution. III. Partial rate factors for the acid-catalyzed bromination of tert-butylbenzene by hypobromous acid>, Category: bromides-buliding-blocks, the main research area is .

The products of acid-catalyzed reaction of tert-BuPh (I) with HOBr in 50% aqueous dioxane were determined, by isotopic dilution, as 37.7% o- (II), 7.2%, m- (III), and 53.2% p-BrC6H4Bu-tert (IV), and 1.9% PhBr (V). Negligible side chain substitution accompanied the reaction, the kinetic form of which was -d[BrOH]/dt = k[ArH][BrOH][H+], with k = 435 1.2 mole-2 min.-1 at 25°, 12 times greater than for C6H6. These results showed that, in a comparison of I with PhMe, the p-position was less reactive, and the m-position was about equally reactive. Significant electrophilic displacement of the tert-Bu group by Br occurred during the reaction. The results were discussed with special reference to the hyperconjugative power of alkyl groups, and to the effect of steric hindrance in determining the reactivity of the o-position. Some nitro derivatives of II, III, and IV were described. III b10 95-7°, nD25 1.5335 and II, b14 102°, nD25 1.5410. II heated at 80° with 1.5 equivalents 98% HNO3 in a mixture of 35% volume/volume H2SO4 and AcOH and the product chromatographed in C6H6 on Al2O3 gave 2,5-Br(O2N)C6H3Bu-tert (VI). The position of the NO2 group was proved as follows: VI (7.5 g.) heated 50 hrs. at 160° with 30% HNO3 in 3 sealed tubes gave about 3% 2,5-Br(O2N)C6H4CO2H, m. 181°. Model experiments showed that 2,4-Br(O2N)C6H3Bu-tert was similarly oxidized to 2,4-Br(O2N)C6H4CO2H, m. 166°. III heated at 80° with 2 equivalents HNO3 in H2SO4435AcOH similarly gave 30% 5,2 (?),4-Br(O2N)2C6H2Bu-tert, m. 92° (from C5H12). IV (5 g.) similarly heated 6 hrs. at 80° under the same nitrating conditions gave a small yield of p-BrC6H4NO2, m. 124°. In the study of the kinetics of bromination the following was a typical run: from a mixture of I (0.00564M), 0.0028M HOBr, and 0.0221M HClO4 in 50% dioxane, aliquot parts were removed at intervals for titration. A blank run with I omitted was made side by side with this measurement. The mean value of k was found to be 435 l.2 mole-2 min.-1 Labeled IV was prepared, NH4Br82 being first shaken with the Br used in the reaction. The product had f.p. 15.7°. To a solution of 10 l. HOBr and 0.05M HClO4 in 50% dioxane was added 19.18 g. I, then 2.37 g. labeled IV was added to the mixture, the mixture extracted with Et2O, and the IV crystallized to give by calculation 9.19 g. IV. Similarly it was shown that 0.308 g. II had been produced in the reaction. III was treated as for II. The mixture contained 0.843 g. active bromo-tert-butylbenzenes, to which was added 11.45 g. inactive III, and the mixture counted, showing that 0.0606 g. III was produced in the reaction. To a mixture which should have contained 1.36 g. mixed active bromo-tert-butylbenzenes was added 12.74 g. V; the mixture extracted, the product nitrated for 2-3 hrs. at 80°, and the product recovered and chromatographed showed that the reaction mixture contained 0.0197 g. V. The conclusion that there was greater hindrance to the entry of NO2 than of Br o- to an alkyl group, was confirmed by this investigation. For I the rate ratios were 0.37 and 0.07, resp., and the free energy difference corresponding to these figures was 0.87 kcal./mole. The effects of hyperconjugation in PhMe and I were considered in some detail. The small proportion of V (1.9 mole-%) determined in the products of bromination was considered significant. The absolute rate of displacement of a tert-Bu group from I was faster than that of displacement of a proton from C6H8.

Journal of the Chemical Society published new progress about Bromination. 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary