- Scalable synthesis of hydroxymethyl alkylfuranoates as stable 2,5-furandicarboxylic acid precursors
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Hydroxymethyl furanoic acid and its derivatives have been synthesized in high yields and purity from gluconolactone. The reaction sequence allows the recovery of reagents and the use of bio-friendly chemicals and solvents, and can easily be scaled up. The reaction product on a >100 gram scale can be purified by a single purification method, such as distillation or precipitation. The overall yield is above 50%.
- Jurys, Arminas,Pedersen, Christian Marcus,Pedersen, Martin J?ger
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- Discovery of Novel and Potent N-Methyl- d -aspartate Receptor Positive Allosteric Modulators with Antidepressant-like Activity in Rodent Models
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N-Methyl-d-aspartate receptors (NMDARs) are glutamate-gated Na+ and Ca2+-permeable ion channels involved in excitatory synaptic transmission and synaptic plasticity. NMDAR hypofunction has long been implicated in the pathophysiology including major depressive disorders (MDDs). Herein, we report a series of furan-2-carboxamide analogues as novel NMDAR-positive allosteric modulators (PAMs). Through structure-based virtual screen and electrophysiological tests, FS2921 was identified as a novel NMDAR PAM with potential antidepressant effects. Further structure-activity relationship studies led to the discovery of novel analogues with increased potentiation. Compound 32h caused a significant increase in NMDAR excitability in vitro and impressive activity in the forced swimming test. Moreover, compound 32h showed no significant inhibition of hERG or cell viability and possessed a favorable PK/PD profile. Our study presented a series of novel NMDAR PAMs and provided potential opportunities for discovering of new antidepressants.
- Li, Zhongtang,Cai, Guanxing,Fang, Fan,Li, Wenchao,Fan, Minghua,Lian, Jingjing,Qiu, Yinli,Xu, Xiangqing,Lv, Xuehui,Li, Yiyan,Zheng, Ruqiu,Wang, Yuxi,Li, Zhongjun,Zhang, Guisen,Liu, Zhenming,Huang, Zhuo,Zhang, Liangren
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p. 5551 - 5576
(2021/05/31)
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- SYNTHESIS OF PRECURSORS OF 2,5-FURANDICARBOXYLIC ACID
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The present invention relates to a method for the manufacture of stable FDCA precursors from saccharide derived starting materials. More specific the invention relates to the synthesis of FDCA precursors such as alkyl 5-(hydroxymethyl)furan-2-carboxylates or 5-(hydroxymethyl)furan-2-carboxylic acid in an expedient, practical and environmental benign manner from e.g. D-glucono-δ-lactone. These bio-based monomer building blocks hold great potential in the manufacture of polymer materials.
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Page/Page column 25; 26
(2019/10/01)
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- Synthesis, preliminary biological evaluation and molecular modeling of some new heterocyclic inhibitors of TACE
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Central heteroaryl ring analogues belonging to a series of potent hydroxamate TACE inhibitors were synthesized. The TACE inhibitory activities of these compounds were evaluated by in vitro WBA and in silico molecular modeling studies using crystal structure of human TACE. Compound 14 showed very good in vitro inhibition, supported by the in silico docking studies.
- Sengupta, Prabal,Puri, Chetan S.,Chokshi, Hemant A.,Sheth, Chetana K.,Midha, Ajay S.,Chitturi, Trinadha Rao,Thennati, Rajamannar,Murumkar, Prashant R.,Yadav, Mange Ram
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experimental part
p. 5549 - 5555
(2011/12/15)
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- FURAN DERIVATIVES FOR PREVENTING AND CURING OSTEOPOROSIS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
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The present invention relates to furan derivatives and pharmaceutical compositions containing them to prevent and cure osteoporosis. The furan derivatives of the present invention have effect on bone proliferation with the side effect reduced, so that they can be used for bone disease.
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Page/Page column 6
(2008/12/08)
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- Design, synthesis and biological evaluation of novel compounds with conjugated structure as anti-tumor agents
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A series of hydroxamic acids with conjugated structure was designed and synthesized to explore the possible HDAC subtype selectivity by testing these compounds against recombinant human HDAC1 and HDAC4. The most selective compound resulted 5a, with a SI of 11.9. The enzymatic inhibitory activity of these conjugated compounds was relatively weak; however, some of these compounds showed significant effect in inducing apoptosis. Moreover, the anti-proliferative activity in cancer cells resulted quite promising, especially in the HCT119 cell line.
- Su, Hong,Nebbioso, Angela,Carafa, Vincenzo,Chen, Yadong,Yang, Bo,Altucci, Lucia,You, Qidong
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p. 7992 - 8002
(2008/12/23)
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- 2-(guanidiniocarbonyl)furans as a new class of potential anion hosts: Synthesis and first binding studies
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The synthesis of a new class of potential anion hosts, the 2-(guanidiniocarbonyl)furans 5a-d, is presented in this study. The facile decomposition of furans under acidic conditions makes the synthesis of these compounds challenging. First binding studies showed that the (guanidiniocarbonyl)furans are much more acidic (pKa ≈5.5) than the analogous pyrroles (pKa ≈ 7) previously introduced by us for oxoanion binding in aqueous solvents. Hence, anion binding with the furan derivatives occurs only in acidic solutions below pH = 5. Therefore, carboxylates are not bound efficiently, whereas, for example, the less basic hydrogen sulfate is bound by 5b with an association constant of K = 600 M -1 in aqueous DMSO even in the presence of a large excess of buffer. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Schmuck, Carsten,Machon, Uwe
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p. 4385 - 4392
(2007/10/03)
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- Novel peptides comprising furanoid sugar amino acids for the treatment of cancer
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Anticancer peptides which incorporate furanoid sugar amino acids and compositions made using these peptides are described. Methods for synthesis of the peptides and for preparing the furanoid sugar amino acids are disclosed. The peptides and compositions made using the peptides have pharmacological applications of these peptides especially in the treatment and prevention of cancer and tumors.
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Page/Page column 4
(2010/02/10)
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- NON-PEPTIDE GnRH AGENTS, METHODS AND INTERMEDIATES FOR THEIR PREPARATION
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Non-peptide GnRH agents capable of inhibiting the effect of gonadotropin-releasing hormone are described. Such compounds and their pharmaceutically acceptable salts, multimers, prodrugs, and active metabolites are suitable for treating mammalian reproductive disorders and steroid hormone-dependent tumors as well as for regulating fertility, where suppression of gonadotropin release is indicated. Methods for synthesizing the compounds and intermediates useful in their preparation are also described.
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Page/Page column 59
(2010/02/11)
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- FURAN DERIVATIVES FOR PREVENTING AND CURING OSTEOPOROSIS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
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The present invention relates to furan derivatives and pharmaceutical compositions containing them to prevent and cure osteoporosis. The furan derivatives of the present invention have effect on bone proliferation with the side effect reduced, so that they can be used for bone disease.
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- Cyclic trimer of 5-(aminomethyl)-2-furancarboxylic acid as a novel synthetic receptor for carboxylate recognition
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A novel 18-membered cyclic oligopeptide 1 based on 5-(aminomethyl)-2-furancarboxylic acid (2), is developed as an excellent receptor for carboxylate binding having an association constant of 8.64×103 M-1 for tetrabutylammonium acetate in CD3CN. The synthesis of 1 was achieved by a high-yielding cyclotrimerization reaction of the unfunctionalized furan amino acid 2.
- Chakraborty, Tushar K,Tapadar, Subhasish,Kiran Kumar
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p. 1317 - 1320
(2007/10/03)
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- The structure of a by-product obtained during the chloromethylation of methyl 2-furoate
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The structure of a crystalline by-product obtained during the chloromethylation of methyl 2-furoate 1 has been established as 1,1-bis(2'- methoxyfuroyl-5'-methylenoexy) methane 5.
- Finan, Patrick A.,Lardner, Caroline M.,O'Sullivan, Paul T.
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- Antimuscarinic agents: Furan analogs of benzilate esters
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The methiodide and ethiodide salts of 5-(dimethylaminomethyl)- and 5-(diethylaminomethyl)-α,α-diphenylfurfuryl alcohol were prepared. These compounds may be considered as furan analogs of dialkylaminoethyl benzilate alkiodides. The pA2 values of these compounds as antagonists of acetylcholine were determined on rat jejunum preparation. All four compounds were significantly less potent than the analogous ester antimuscarinic lachesine. The furan ring cannot be substituted for the ester moiety of typical antimuscarinics. Possible modes of binding by antagonists to the receptor proposed previously are considered that might account for this less-than-expected antimuscarinic activity.
- Stubbins,Hudgins,Murphy
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p. 534 - 537
(2007/10/02)
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