- Quinoline-Proline, Triazole Hybrids: Design, Synthesis, Antituberculosis, Molecular Docking, and ADMET Studies
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A series of novel quinoline-proline hybrids (11a-g) and quinoline-proline-1,2,3-triazole hybrids (12-14) were synthesized by click chemistry based on molecular hybridization concept and were characterized by NMR, mass spectrometry, and elemental analysis. All the titled target compounds were tested for antitubercular activity by MABA and LORA methods by in vitro. Interestingly, two compounds (2R,4S)-1-((2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl)-methyl)-4-(4-nitrobenzamido)-N-phenylpyrrolidine-2-carboxamide (11b) and (2R,4S)-1-((2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl)-methyl)-4-(4-fluorobenzamido)-N-phenylpyrrolidine-2-carboxamide (11c) exhibited significant activity against the tested Mycobacterium tuberculosis H37Rv strain. Further, the cytotoxicity (CC50) profile of the titled compounds against the Vero cell was performed and discussed. A molecular docking study of the hit compounds (11b and 11c) was also performed to find their putative binding interaction with the active site of the target proteins. Finally, in silico ADMET properties were also predicted for all the synthesized molecules to evaluate their drug-likeness behavior.
- Ganesan, Moorthiamma Sarathy,Raja, Kamatchi Kanmani,Murugesan, Sankaranarayanan,Karankumar, Banoth,Faheem, Faheem,Thirunavukkarasu, Sappanimuthu,Shetye, Gauri,Ma, Rui,Franzblau, Scott G.,Wan, Baojie,Rajagopal, Gurusamy
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- DERIVATIVES OF PIPERLONGUMINE AND USES THEREOF
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The present invention relates to a group of 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one (piperlongumine) derivatives, analogs and pharmaceutically acceptable salts thereof. The present invention also relates to a pharmaceutical composition and formulation containing a derivative of piperlongumine; and use of the derivatives and analogs for treating cancer, reducing inflammation and/or treating an autoimmune or inflammatory disease.
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Paragraph 0534-0535; 0698-0699
(2020/12/13)
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- DERIVATIVES OF PIPERLONGUMINE AND USES THEREOF
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The present invention relates to a group of 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3- dihydropyridin-6-one (piperlongumine) derivatives, analogs and pharmaceutically acceptable salts thereof. The present invention also relates to processes for preparing the same; a pharmaceutical composition and formulation containing a derivative of piperlogumine; and use of the derivatives and analogs for treating cancer.
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Page/Page column 122; 123; 159; 160
(2019/06/11)
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- Anhydrides from aldehydes or alcohols via oxidative cross-coupling
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A novel type of metal-free oxidative cross-coupling for the synthesis of symmetrical and mixed anhydrides from aldehydes or benzylic alcohols has been developed. The aldehydes or alcohols were converted in situ into their corresponding acyl chlorides, which were then reacted with an array of carboxylic acids. The methodology has a general applicability, and was successfully employed to prepare either aromatic or aliphatic symmetrical anhydrides and mixed anhydrides, which are very unstable compounds.
- Gaspa, Silvia,Amura, Ida,Porcheddu, Andrea,De Luca, Lidia
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p. 931 - 939
(2017/02/10)
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- Direct inter- and intramolecular addition of amides to arylalkenes promoted by KOt-Bu/DMF
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Direct addition of tetrahydroisoquinoline derived amides to arylalkenes has been achieved in the presence of KOt-Bu/DMF. Both intermolecular and intramolecular reactions could occur in good yields. α-Amido alkyl radicals are proposed to be generated under the reaction conditions. The reaction is efficient for the synthesis of seven-membered nitrogen heterocycles. A homoprotoberberine was prepared conveniently via this method.
- Wang, Wei-Juan,Zhao, Xu,Tong, Lang,Chen, Jia-Hua,Zhang, Xue-Jing,Yan, Ming
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p. 8557 - 8565
(2015/01/08)
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- Thermodynamic and kinetic considerations in the chemoselective O-acylation by mixed anhydrides. A semiempirical MO approach
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A simple methodology to achieve high chemoselective O-acylation of primary hydroxy groups, in the presence of secondary ones, was performed by means of the quick generation of a mixed anhydride using mild and inexpensive conditions. Steric and electronic
- Mota, Antonio J.,Robles, Rafael,De Cienfuegos, Luis álvarez,Lamenca, Alberto
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p. 3349 - 3353
(2007/10/03)
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- Reaction of piperazine with trimethylacetic arylcarboxylic anhydride; a convenient method for preparing monoacylated piperazine derivatives
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A series of monosubstituted piperazine derivatives were obtained by the reaction of piperazine with trimethylacetic arylcarboxylic anhydrides in good yields, which were prepared in situ from arylcarboxylic acid with trimethylacetyl chloride in the presence of triethylamine.
- Lai,Wang,Luh
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p. 361 - 363
(2007/10/03)
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- Synthesis of prolyl endopeptidase inhibitors and evaluation of their structure-activity relationships: In vitro inhibition of prolyl endopeptidase from canine brain
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By chemical modification of a known prolyl endopeptidase (PEP) inhibitor (N-[N-(4-phenylbutanoyl)-L-prolyl]pyrrolidine; SUAM-1221), several arylalkanoyl derivatives (V-1-27) were synthesized and tested for in vitro inhibitory activity towards PEP from canine brain. Among them, 4-(2- thienyl)butanoyl derivatives (V-24-27) showed more potent PEP-inhibitory activity than SUAM-1221. The structure-activity relationships of these compounds are discussed.
- Arai,Nishioka,Niwa,Yamanaka,Tanaka,Yoshinaga,Kobayashi,Miura,Ikeda
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p. 1583 - 1588
(2007/10/02)
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- PHASE MANAGED ORGANIC SYNTHESIS 2. A NEW POLYMER ASSISTED SYNTHESIS OF ACID ANHYDRIDES.
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A solid-phase copolymer of 4-vinylpyridine is shown to be a highly effective reagent/catalyst for the synthesis of acid anhydrides from mixtures containing equimolar quantities of carboxylic acid and acid chlorides.The process may be carried out in batch or column mode.
- Fife, Wilmer K.,Zhang, Zhi-dong
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p. 4933 - 4936
(2007/10/02)
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- Reaction of Diazonium Salts with Transition Metals. 6. Preparation of Mixed Acid Anhydrides from Arenediazonium Salts and Sodium Carboxylates under Palladium(0) Catalysis
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The palladium(0)-catalyzed reaction of arenediazonium tetrafluoroborates with carbon monoxide and sodium carboxylates in acetonitrile at 25 deg C gave mixed acid anhydrides, ArCOOCOR (Ar = 3-Me-Ph, 4-Me-Ph, 2-MeO-Ph, 4-Br-Ph, 4-I-Ph, 3-NO2-Ph, 4-NO2-Ph, and Ph; R = H, Me, Et, t-Bu, and Ph) in good yields.Homoaromatic acid anhydrides, (ArCO)2O, were obtained by heating of ArCOOCOMe at 100-120 deg C under vacuum.ArCOOCO-t-Bu can be utilized to obtain the corresponding arenecarboxamides by the reaction with some amines.
- Kikukawa, Kiyoshi,Kono, Kiyoshi,Nagira, Kazuhiko,Wada, Fumio,Matsuda, Tsutomu
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p. 4413 - 4416
(2007/10/02)
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