- CYCLOALKYL-CONTAINING CARBOXYLIC ACIDS AND USES THEREOF
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The present application discloses a compound of formula (I) or a salt thereof: (I) and compositions comprising such compound or salt thereof. The use of such compound, salt thereof or composition comprising same for treating anemia or leukopenia, fibrosis, cancer, hypertension and/or a metabolic condition in a subject is also disclosed.
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Page/Page column 63; 64
(2021/06/26)
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- Synthesis of 3-alkyl(aryl)thietanes
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A preparative procedure for the synthesis of thietanes bearing alkyl substituents in the β-position was developed. Using this procedure, 3-substituted thietanes can be obtained in four steps with an ultimate yield of > 50%. 3-R-thietanes (where R = CH3, C4H9, C5H11, C6H13, C6H 5) and the corresponding sulfoxides and sulfones were synthesized and examined. The feasibility of preparation of gem-3,3-substituted thietanes was exemplified by the synthesis of 3,3-dihexylthietane.
- Shevchenko,Volynskii
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body text
p. 123 - 128
(2010/02/28)
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- Stereocontrolled alkylative construction of quaternary carbon centers
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Protocols for the stereodefined formation of α,α-disubstituted enolates of pseudoephedrine amides are presented followed by the implementation of these in diastereoselective alkylation reactions. Direct alkylation of α,α-disubstituted pseudoephedrine amide substrates is demonstrated to be both efficient and diastereoselective across a range of substrates, as exemplified by alkylation of the diastereomeric pseudoephedrine α-methylbutyramides, where both substrates are found to undergo stereospecific replacement of the α-C-H bond with α-C-alkyl, with retention of stereochemistry. This is shown to arise by sequential stereospecific enolization and alkylation reactions, with the alkyl halide attacking a common π-face of the E- and Z-enolates, proposed to be opposite the pseudoephedrine alkoxide side chain. Pseudoephedrine α-phenylbutyramides are found to undergo highly stereoselective but not stereospecific α-alkylation reactions, which evidence suggests is due to facile enolate isomerization. Also, we show that α,α-disubstituted pseudoephedrine amide enolates can be generated in a highly stereocontrolled fashion by conjugate addition of an alkyllithium reagent to the s-cis-conformer of an α-alkyl-α,β-unsaturated pseudoephedrine amide, providing α,α-disubstituted enolate substrates that undergo alkylation in the same sense as those formed by direct deprotonation. Methods are presented to transform the α-quaternary pseudoephedrine amide products into optically active carboxylic acids, ketones, primary alcohols, and aldehydes. Copyright
- Kummer, David A.,Chain, William J.,Morales, Marvin R.,Quiroga, Olga,Myers, Andrew G.
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supporting information; experimental part
p. 13231 - 13233
(2009/02/06)
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- Peptide deformylase inhibitors of Mycobacterium tuberculosis: Synthesis, structural investigations, and biological results
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Bacterial peptide deformylase (PDF) belongs to a subfamily of metalloproteases catalyzing the removal of the N-terminal formyl group from newly synthesized proteins. We report the synthesis and biological activity of highly potent inhibitors of Mycobacterium tuberculosis (Mtb) PDF enzyme as well as the first X-ray crystal structure of Mtb PDF. Structure-activity relationship and crystallographic data clarified the structural requirements for high enzyme potency and cell based potency. Activities against single and multi-drug-resistant Mtb strains are also reported.
- Pichota, Arkadius,Duraiswamy, Jeyaraj,Yin, Zheng,Keller, Thomas H.,Alam, Jenefer,Liung, Sarah,Lee, Gladys,Ding, Mei,Wang, Gang,Chan, Wai Ling,Schreiber, Mark,Ma, Ida,Beer, David,Ngew, Xinyi,Mukherjee, Kakoli,Nanjundappa, Mahesh,Teo, Jeanette W.P.,Thayalan, Pamela,Yap, Amelia,Dick, Thomas,Meng, Wuyi,Xu, Mei,Koehn, James,Pan, Shi-Hao,Clark, Kirk,Xie, Xiaoling,Shoen, Carolyn,Cynamon, Michael
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scheme or table
p. 6568 - 6572
(2009/09/30)
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- Structure-retention relationship in a series of chiral 1,4-disubstituted piperazine derivatives on carbohydrate chiral stationary phases
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New racemic 1,4-disubstituted piperazines chemically named ethyl 2-[(4-pyrimidin-2yl-piperazine-1yl)carbonyl]C3-C5-alkanoates 1-7 were synthesized. The compounds were resolved into enantiomers on cellulose tris(4-methylbenzoate) and amylose tris(3,5-dimethylphenylcarbamate) stationary phases using hexane/propan-2-ol mobile phases. The optimum separation conditions for the compounds were obtained on cellulose tris(4-methylbenzoate) with 5% of 2-propanol in hexane. The relationship between structural and chromatographic parameters is discussed.
- Chilmonczyk, Zdzislaw,Sienicki, Lukasz,Lozowicka, Bozena,Lisowska-Kuzmicz, Malgorzata,Jonczyk, Anna,Aboul-Enein, Hassan Y.
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p. 439 - 443
(2007/10/03)
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- Synthesis and characterization of 6-O-acyl-2-O-α-D-glucopyranosyl-L- ascorbic acids with a branched-acyl chain
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We previously reported the chemical synthesis of a series of novel monoacylated vitamin C derivatives, 6-O-acyl-2-O-α-D-glucopyranosyl-L- ascorbic acids (6-Acyl-AA-2G) possessing a straight-acyl chain of varying length from C4 to C18, as effective skin antioxidants. In this paper, we describe branched type of 6-Acyl-AA-2G derivatives (6-bAcyl-AA-2G) synthesized by use of a 2-branched-chain fatty acid anhydride as an acyl donor. The stability of 6-bAcyl-AA-2G in neutral solution was much higher than that of 6-Acyl-AA-2G, while they were susceptible to enzymatic hydrolysis for exerting vitamin C effect. These branched derivatives as well as 6-Acyl-AA-2G increased the radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl and the lipophilicity in octanol/water-partitioning systems with increasing length of their acyl group. In addition, the 6-bAcyl-AA-2G derivative with an acyl chain of C12, 6-bDode-AA-2G had the excellent solubility to various solvents, suggesting easy handling in cosmetic use. These characteristics of 6-bAcyl-AA-2G may be available for skin care application as an effective antioxidant.
- Tai, Akihiro,Kawasaki, Daisuke,Sasaki, Kenji,Gohda, Eiichi,Yamamoto, Itaru
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p. 175 - 180
(2007/10/03)
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- Preparation of phosphinodipeptide analogs as building blocks for pseudopeptides synthesis
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A simple and effective preparation of phosphinodipeptides, in good overall yields, has been developed. This one pot procedure, allowing the variation of the substituents in α and/or β position to the phosphorus atom and also in α position to the nitrogen atom, consists in the addition of alkyl hypophosphites to imines, followed by Michael-addition on acrylates. To show the value of phosphinodipeptides analogs 1 as synthetic intermediates, selective deprotections of the three functional groups are described.
- Cristau, Henri-Jean,Coulombeau, Agnès,Genevois-Borella, Arielle,Sanchez, Frédéric,Pirat, Jean-Luc
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p. 381 - 391
(2007/10/03)
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- Synthesis of a tetraamido macrocycle ligand from a novel diamidodiol
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A new composition of matter for a diamidodiol and a method for preparing the diamidodiol. The exemplary diamidodiol has the formula C15H30N2O4 and is prepared by reacting a first quantity of 2-amino-2-methyl-1-propanol with a second quantity of a di-substituted malonyl dichloride (i.e., diethylmalonyl dichloride), preferably in ethyl acetate as solvent. A tetraamido macrocycle is prepared from the diamidodiol in two steps by oxidizing the diamidodiol to form a diacid followed by coupling using a known procedure of the diacid with an aryl diamine (e.g., 1,2-diaminobenzene) to yield the tetraamido macrocycle.
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Page column 5
(2010/02/05)
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- The synthesis and electro-optic properties of liquid crystalline 2- (2,3-difluorobiphenyl-4'-yl)-1,3-dioxanes
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Fifty-six novel alkyl and/or alkoxy disubstituted 2-(2,3- difluorobiphenyl-4'-yl)-1,3-dioxanes (DFBPD) were prepared. Smectic C and nematic mesophases were exhibited by most of the alkyl-alkoxy homologues. Conversely, most of the dialkyl compounds exhibited smectic C, smectic A and nematic phases. The birefringence (Δn), dielectric anisotropy (Δε), spontaneous polarisation and response times of two ferroelectric mixtures formulated from the dioxanyl systems were determined. The birefringence results were compared with eight other groups of mixtures where the materials were based on different core systems. The overall electro-optic properties of the DFBPDs were found to be comparable to the best of the eight most commonly used materials in ferroelectric display devices.
- Dong, Chu Chuan,Styring, Peter,Goodby, John W.,Chan, Lawrence K. M.
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p. 1669 - 1677
(2007/10/03)
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- Direct preparation of allylstannanes from allyl alcohols: Convenient synthesis of β-substituted allylstannanes and of stereodefined γ-substituted allylstannanes
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Primary allyl alcohols are converted into allyltributylstannanes in a one-pot operation. It entails (i) deprotonation with BuLi, (ii) sulfonylation with mesyl chloride, and (iii) nucleophilic substitution by LiSnBu3. Conversions are quantitative with isolated yields ranging from 70% to 100%. If the starting allyl alcohol contains a stereogenic double bond its configuration is retained.
- Weigand, Stefan,Brueckner, Reinhard
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p. 475 - 482
(2007/10/03)
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- 1,3-dioxane derivative and liquid crystal compositions containing it
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A 1,3-dioxane derivative and a liquid crystal composition containing it as expressed by the general formula STR1 (where R is a straight chain alkyl group of carbon number 1 to 10, A is a single bond or --CH2 CH2 -- group, n is 0 or 1, and the cyclohexane ring and 1,3-dioxane ring are respectively in trans form is disclosed.) The 1,3-dioxane derivative represented by general formula (I) has a very large dielectric anisotropy and a small birefringence. Liquid crystal compositions containing (I) can be driven at low voltage and will provide a liquid crystal display apparatus with a wide visual angle.
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- 1,3-dioxane derivatives and composition including same
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2-(3', 4'-difluorophenyl)-1,3-dioxane derivatives represented by the general formula: STR1 wherein R is a linear alkyl group having from 1 to 8 atoms, and having large positive dielectric constant anisotropy (Δε) and small refractive index anisotropy (Δn). The dioxane derivatives may be included in liquid crystal compositions for improved display devices having a low threshold voltage, a low driving voltage and a wide visual angle.
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- Synthesis and Liquid Crystal Properties of Dimethylene Linked Compounds Incorporating the Cyclobutane or Spiroheptane Rings
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The preparation of sixteen dimethylene linked compounds is described heptane ring>, and a comparison is made between the transition temperatures of these compounds and those of the corresponding esters.This comparison once again highlights the fact that the cyclobutane ring should be regarded, in terms of its ability to promote nematic thermal stability, as a "chain stiffener rather than as a ring system.A comparison is also made of the nematic thermal stabilities of the trans-cyclobutane and the spiroheptane systems and of the trans-cyclohexane and the spiroundecane systems.
- Chan, L. K. M.,Gemmell, P. A.,Gray, G. W.,Lacey, D.,Toyne, K. J.
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p. 229 - 246
(2007/10/02)
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- ALKYLATION OF MALONIC ESTER AND MONOALKYLMALONIC ESTERS UNDER THE CONDITIONS OF PHASE-TRANSFER CATALYSIS
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Simple procedures were developed for the monoalkylation of malonic ester in the potassium hydroxide-DMFA (DMFA-acetone)-triethylbenzylammonium chloride system and the alkylation of alkylmalonic esters to dialkylmalonic esters in the calcium oxide-DMFA system.
- Sukhanov, N. N.,Trappel', L. N.,Chetverikov, V. P.,Yanovskaya, L. A.
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p. 2288 - 2290
(2007/10/02)
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- LIQUID CRYSTAL MATERIALS WITH SULFUR ATOMS INCORPORATED IN THE PRINCIPAL STRUCTURE: 1. NEW LIQUID CRYSTAL COMPOUNDS WITH 1,3-DITHIANE RING.
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2-(p-Substituted phenyl)-5-alkyl-1,3-dithianes, new liquid crystals, were synthesized by the thioacetalization of the corresponding aldehydes and dithiols. These compounds have characteristic supercooling states, exhibit monotropic liquid crystal phases even in the case of long terminal alkyl substituents. The mesomorphic characteristics of these compounds were different from those of the corresponding 1,3-dioxanes, this must originate in the difference in the molecular width caused by the difference in the atomic volume between sulfur and oxygen.
- Haramoto,Nobe,Kamogawa
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p. 1966 - 1969
(2007/10/02)
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- The Reactivity of Carbenes from Photolysis of Diazo-Compounds towards Carbon-Hydrogen Bonds. Effects of Structure, Temperature, and Matrix on the Insertion Selectivity
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Direct and/or sensitized photolyses of diazo-acetate (1a) and -malonate (1b) in hydrocarbons and ether were investigated at various temperatures in order to learn more about the nature of the C-H insertion process and the structural factors governing positional selectivity within the matrix.Photolysis of the diazo-compounds in a rigid matrix resulted in a marked decrease in the insertion selectivity, which may be interpreted as indicating that the matrix imposes severe steric demand especially on the direct C-H insertion process of the singlet carbene.The addition of a sensitizer in matrix photolysis causes a marked increase in the selectivity in the case of (1a), as is observed in the comparable liquid-phase experiment, but it causes a decrease in the case of (1b).This is interpreted as suggesting that the excited triplet (1b) itself is involved in C-H insertion under these conditions.More extensive temperature studies show that, as the temperature decreases, the C-H insertion selectivity of :CHCO2R decreases regularly regardless of the reaction phase, whereas that of :C(CO2R)2 increases in the liquid phase but decreases in the solid phase.This difference in the temperature dependence is explained by assuming that the singlet carbene is responsible for the C-H insertion of :CHCO2R throughout the temperature range studied, while both singlet and triplet are involved in the insertion of :C(CO2R)2.
- Tomioka, Hideo,Itoh, Masami,Yamakawa, Shyoji,Izawa, Yasuji
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p. 603 - 609
(2007/10/02)
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