- Synthesis of novel of 2, 5-disubstituted 1, 3, 4- oxadiazole derivatives and their in vitro anti-inflammatory, anti-oxidant evaluation, and molecular docking study
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A series of novel 2, 5-disubstituted 1, 3, 4-Oxadiazole derivatives as a potential anti-inflammatory, and anti-oxidant agent were synthesized via cyclisation. Hydrazide molecule treated with substituted acids in the presence of phosphorus oxychloride (POCl3) as an efficient reagent as well as solvent by conventional method with shorter reaction time and excellent yield. The newly synthesized 1, 3, 4- oxadiazole derivatives exhibited excellent to good anti-inflammatory and anti-oxidant activities compaired to the standard drugs. Molecular docking study on the crucial anti-inflammatory target–cyclooxygenase-2 (COX-2) revealed the ability of the scaffold to correctly recognize the active site and achieve significant bonded and non-bonded interactions with key residues therein. This study could identify potential compounds which can be pertinent starting points for structure-based drug design to obtain newer anti-inflammatory agents.
- Dongare, Balasaheb B.,Ghanwat, Anil A.,Kashid, Bharat B.,Khedkar, Vijay M.,More, Kishor R.,Salunkhe, Pravin H.
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- Preparation method of 3,4-dihydro-2H-1-benzopyran-2-carboxylic acid compound and application thereof
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Disclosed are a preparation method of a 3,4-dihydro-2H-1-benzopyran-2-carboxylic acid compound and application thereof. The invention relates to the field of organic synthesis. According to the method, a phenolic compound is reacted with a gamma-butyrrolactone compound under the action of alkalis to obtain an intermediate; ring-closing reaction is conducted on the intermediate under the action ofacid catalysts, and the 3,4-dihydro-2H-1-benzopyran-2-carboxylic acid compound is obtained with high efficiency and high yield only by two simple steps of reaction; the preparation method has the advantages of being simple in routine design and procedures, convenient to operate and low in cost, and the method is very suitable for industrialized large-scale production; by applying the preparation method of the 3,4-dihydro-2H-1-benzopyran-2-carboxylic acid compound to the application for preparing medicines with the structure of 3,4-dihydro-2H-1-benzopyran-2-carboxylic acid, the yield of the medicines can be improved and the production cost can be reduced.
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- Preparation method of chromanone 2-carboxylic acid or chroman 2-carboxylic acid derivatives
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The present invention relates to a chromanone-2-carboxylic acid derivative and a chroman-2-carboxylic acid derivative which can be used as an intermediate for effective medicinal components currently available in the market, and to preparation methods the
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- 6-fluoro-chroman-2-carboxylic acid
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The invention discloses a preparation method of 6- fluorochroman-2-formic acid. The method comprises the following steps: with p-fluorophenol and dimethyl acetylenedicarboxylate as initial raw materials, carrying out an addition reaction on p-fluorophenol and dimethyl acetylenedicarboxylate to generate dimethyl 2-(p-fluorophenoxy) acetylenedicarboxylate, hydrolyzing under an alkaline condition to generate 2-(p-fluorophenoxy) butenedioic acid, dissolving obtained 2-(p-fluorophenoxy) butenedioic acid in concentrated sulfuric acid to perform cyclization to generate 6-fluoro-4-oxo-4H-1-benzopyran-2-formic acid, and finally, carrying out pressurized hydrogenation catalytic reduction to obtain 6-fluorochroman-2-formic acid. The method disclosed by the invention has the advantages of simple operation, low cost and high product yield, and reactions in the steps are safe and environment-friendly, so that the method is especially suitable for industrial production.
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- An efficient and practical enantiospecific synthesis of methyl chromanone- and chroman-2-carboxylates
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Chromanone-2-carboxylates and chroman-2-carboxylates are useful building blocks for the synthesis of a variety of bioactive compounds, such as repinotan, fidarestat, and nebivolol. An efficient and practical enantiospecific synthesis of chromanone-2-carboxylates and chroman-2-carboxylates has been accomplished using intramolecular Mitsunobu etherification of methyl (S)-2-hydroxy-4-oxo-4-(2′-hydroxy)phenylbutanoates derived from l-malic acid.
- Kim, Dong Woon,Maqusood Alam,Lee, Young Hun,Khan, M. Naseer A.,Zhang, Yong,Lee, Yong Sup
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p. 912 - 917
(2015/08/24)
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- Enantioselective copper-catalyzed intramolecular phenolic O-H bond insertion: Synthesis of chiral 2-carboxy dihydrobenzofurans, dihydrobenzopyrans, and tetrahydrobenzooxepines
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Efficient: A copper-catalyzed enantioselective intramolecular insertion of carbenoids into phenolic O-H bonds has been developed. This method can be used for the synthesis of the title compounds in high yields and excellent enantioselectivities under mild and neutral conditions (see scheme). NaBAr F=sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Copyright
- Song, Xiao-Guang,Zhu, Shou-Fei,Xie, Xiu-Lan,Zhou, Qi-Lin
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supporting information
p. 2555 - 2558
(2013/04/10)
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- Iridium-catalyzed enantioselective hydrogenation of unsaturated heterocyclic acids
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Spiral binding: A highly enantioselective hydrogenation of unsaturated heterocyclic acids has been developed by using chiral iridium/spirophosphino oxazoline catalysts (see scheme; BArF-=tetrakis[3,5- bis(trifluoromethyl)phenyl]borate, Boc=tert-butoxycarbonyl). This reaction provided an efficient method for the preparation of optically active heterocyclic acids with excellent enantioselectivities. Copyright
- Song, Song,Zhu, Shou-Fei,Pu, Liu-Yang,Zhou, Qi-Lin
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p. 6072 - 6075
(2013/07/05)
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- PROCESS FOR THE PREPARATION OF NEBIVOLOL
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The present invention relates to a novel process for the synthesis of the Nebivolol product depicted in Scheme 1, comprised of a reduced number of high-yield steps, and characterized by the enzymatic resolution of the chroman ester precursor.
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Page/Page column 16-18
(2012/07/28)
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- A mild synthesis of α,α′-[iminobismethylene]bis[6-fluoro- 3,4-dihydro-2H-1 -benzopyran-2-methanol]
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A new synthesis of α,α′-[iminobismethylene]bis[6-fluoro- 3,4-dihydro-2H-1-benzopyran-2-methanol (1) is described, with most reactions being carried out at room temperature and normal pressure, that will further contribute to the development of new scalable synthesis of the related drug substance of Nebivolol (overall yield: 33%).
- Bai, Yihui,Chen, Xinzhi
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p. 807 - 808
(2007/10/03)
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- NEBIVOLOL AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS, PROCESS FOR PREPARATION AND PHARMACEUTICAL COMPOSITIONS OF NEBIVOLOL
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The present invention provides an improved process for the synthesis of nebivolol or its pharmaceutically acceptable salts, more particularly hydrochloride salt of formula (I). The present invention further provides a new Form T1 of nebivolol and its pharmaceutically acceptable salts. The present invention also provides pharmaceutical compositions and process for the preparation of a solid oral dosage form of nebivolol hydrochloride of formula (I), without the use of wetting agent, and optionally using binder and /or disintegrant.
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Page/Page column 12-13
(2010/10/20)
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- Metabotropic glutamate receptor antagonists
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The present invention concerns compounds of formula. In a preferable embodiment, X represents O; R1 represents C1-6alkyl; cycloC3-12alkyl or (cycloC3-12alkyl)C1-6alkyl, wherein one or more hydrogen atoms in a C1-6alkyl-moiety or in a cycloC3-12alkyl-moiety optionally may be replaced by C1-6alkyloxy, aryl, halo or thienyl; R2 represents hydrogen; halo; C1-6alkyl or amino; R3 and R4 each independently represent hydrogen or C1-6alkyl; or R2 and R3 may be taken together to form —R2-R3-, which represents a bivalent radical of formula -Z4-CH2-CH2-CH2- or -Z4-CH2-CH2- with Z4 being O or NR11 wherein R11 is C1-6alkyl; and wherein each bivalent radical is optionally substituted with C1-6alkyl; or R3 and R4 may be taken together to form a bivalent radical of formula —CH2-CH2-CH2-CH2-; R5 represents hydrogen; Y represents O; and aryl represents phenyl optionally substituted with halo. The invention also relates to the use of a compound according to the invention as a medicament and in the manufacture of a medicament for treating or preventing glutamate-induced diseases of the central nervous system, as well as formulations comprising such a compound and processes for preparing such a compound.
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- Method of lowering the blood pressure
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A method of potentiating the effects of blood pressure reducing agents in warm-blooded animals, said method comprising administering to said warm-blooded animals of an effective amount of a blood pressure reducing agent and a 2,2′-iminobisethanol derivative.
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- DERIVATIVES OF 2,2'-IMINOBISETHANOL
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Derivatives of 2,2'-iminobisethanol having useful properties in the treatment and/or the prevention of disorders of the coronary-vascular system.
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