18327-36-1Relevant academic research and scientific papers
Identification of gallic acid based glycoconjugates as a novel tubulin polymerization inhibitors
Upadhyaya, Kapil,Hamidullah,Singh, Kartikey,Arun, Ashutosh,Shukla, Mahendra,Srivastava, Neetika,Ashraf, Raghib,Sharma, Abhisheak,Mahar, Rohit,Shukla, Sanjeev K.,Sarkar, Jayanta,Ramachandran, Ravishankar,Lal, Jawahar,Konwar, Rituraj,Tripathi, Rama Pati
, p. 1338 - 1358 (2016)
A novel class of gallic acid based glycoconjugates were designed and synthesized as potential anticancer agents. Among all the compounds screened, compound 2a showed potent anticancer activity against breast cancer cells. The latter resulted in tubulin po
Synthesis of gallic acid analogs as histamine and pro-inflammatory cytokine inhibitors for treatment of mast cell-mediated allergic inflammation
Fei, Xiang,Je, In-Gyu,Shin, Tae-Yong,Kim, Sang-Hyun,Seo, Seung-Yong
, (2017)
Gallic acid (3,4,5-trihydroxybenzoic acid), is a natural product found in various foods and herbs that are well known as powerful antioxidants. Our previous report demonstrated that it inhibits mast cell-derived inflammatory allergic reactions by blocking histamine release and pro-inflammatory cytokine expression. In this report, various amide analogs of gallic acid have been synthesized by introducing different amines through carbodiimide-mediated amide coupling and Pd/C-catalyzed hydrogenation. These compounds showed a modest to high inhibitory effect on histamine release and pro-inflammatory cytokine expression. Among them, the amide bearing (S)-phenylglycine methyl ester 3d was found to be more active than natural gallic acid. Further optimization yielded several (S)-and (R)-phenylglycine analogs that inhibited histamine release in vitro. Our findings suggest that some gallamides could be used as a treatment for allergic inflammatory diseases.
Sequential Au/Cu Catalysis: A Two Catalyst One-Pot Protocol for the Enantioselective Synthesis of Oxazole α-Hydroxy Esters via Intramolecular Cyclization/Intermolecular Alder-Ene Reaction
Nalivela, Kumara Swamy,Rudolph, Matthias,Baeissa, Elham S.,Alhogbi, Basma G.,Mkhalid, Ibraheem A. I.,Hashmi, A. Stephen K.
supporting information, p. 2183 - 2190 (2018/04/30)
A convenient protocol for the enantioselective synthesis of oxazole α-hydroxy ester derivatives 4 from readily available propargylamides 1 and alkylglyoxylates 3 was developed. The first step of the one-pot procedure is the selective intramolecular in situ formation of an alkylideneoxazoline 2, which then in an intermolecular reaction is enantioselectively transformed to the oxazole α-hydroxy ester derivatives 4 in quantitative yield and good to excellent enantioselectivity via an asymmetric copper(II)-catalyzed Alder-ene reaction. (Figure presented.).
From propargylic amides to functionalized oxazoles: Domino gold catalysis/oxidation by dioxygen
Hashmi, A. Stephen K.,Blanco Jaimes, Maria Camila,Schuster, Andreas M.,Rominger, Frank
experimental part, p. 6394 - 6408 (2012/09/22)
A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroperoxides bearing the heteroaromatic oxazoles. Experiments addressing the reaction mechanism reveal a radical pathway for this autoxidation process. The hydroperoxides could conveniently be converted to the corresponding alcohols by reduction with sodium borohydride.
Facile, selective, and regiocontrolled synthesis of oxazolines and oxazoles mediated by ZnI2 and FeCl3
Senadi, Gopal Chandru,Hu, Wan-Ping,Hsiao, Jia-Shing,Vandavasi, Jaya Kishore,Chen, Chung-Yu,Wang, Jeh-Jeng
supporting information, p. 4478 - 4481 (2012/10/30)
An expedient method for a direct approach to the selective and regiocontrolled synthesis of 2-oxazolines and 2-oxazoles mediated by ZnI 2 and FeCl3 is described. A Lewis acid promoted cyclization of acetylenic amide with various func
Multifunctional multivalency: A focused library of polymeric cholera toxin antagonists
Tran, Huu-Anh,Kitov, Pavel I.,Paszkiewicz, Eugenia,Sadowska, Joanna M.,Bundle, David R.
experimental part, p. 3658 - 3671 (2011/06/19)
Structural pre-organization of the multivalent ligands is important for successful interaction with multimeric proteins. Polymer-based heterobifunctional ligands that contain pendant groups prearranged into heterodimers can be used to probe the active site and surrounding area of the receptor. Here we describe the synthesis and activities of a series of galactose conjugates on polyacrylamide and dextran. Conjugation of a second fragment resulted in nanomolar inhibitors of cholera toxin, while the galactose-only progenitors showed no detectable activity.
