114628-32-9Relevant articles and documents
Bioinspired Diastereoconvergent Synthesis of the Tricyclic Core of Palodesangrens via Diels-Alder Reaction, LiAlH4-Mediated Isomerization, and Acid-Mediated Cyclization
Songthammawat, Poramate,Wangngae, Sirilak,Matsumoto, Koki,Duangkamol, Chuthamat,Ruchirawat, Somsak,Ploypradith, Poonsakdi
, p. 5225 - 5241 (2018/05/07)
The cyclohexene moiety of the tricyclic 6,7-diaryl-tetrahydro-6H-benzo[c]chromene core of palodesangrens could be assembled in a biomimetic and step-economical fashion by the Diels-Alder reaction between the electron-rich (E)-1,3-butadienylarenes as the diene and the electron-deficient chalcones as the dienophile. During the reduction of ketone to the corresponding alcohol by LiAlH4, the mixture of endo and exo isomers underwent a novel diastereoconvergent LiAlH4-mediated isomerization to install the desired stereochemistry at C10a. Subsequent pyran ring closure under acidic conditions installed the stereochemistry at the remaining C6. Overall, the tricyclic core of palodesangrens could be prepared in three steps and up to 38% yield.
Unified Synthesis of the Marine Sesquiterpene Quinones (+)-Smenoqualone, (–)-Ilimaquinone, (+)-Smenospongine, and (+)-Isospongiaquinone
Katoh, Takeru,Atsumi, Suguru,Saito, Ryo,Narita, Koichi,Katoh, Tadashi
, p. 3837 - 3849 (2017/07/22)
The marine sesquiterpene quinones (+)-smenoqualone, (–)-ilimaquinone, (+)-smenospongine, and (+)-isospongiaquinone were efficiently synthesized in a unified manner starting from a known trans-decalin derivative, which is accessible from (+)-5-methyl Wiela
Compound having acyl coa:cholesterol acyltransferase inhibitory and composition for prevention or treatment of cardiovascular disease comprising thereof
-
Paragraph 0068-0069, (2017/08/08)
The present invention relates to: a compound denoted by chemical formula 1 or pharmaceutically acceptable salt thereof; and a composition for preventing or treating cardiovascular diseases containing the same as an effective component. The compound or the
Design, synthesis and docking study of 5-(substituted benzylidene) thiazolidine-2,4-dione derivatives as inhibitors of protein tyrosine phosphatase 1B
Wang, Zengtao,Liu, Zhiguo,Lee, Woojung,Kim, Su-Nam,Yoon, Goo,Cheon, Seung Hoon
, p. 3337 - 3340 (2014/07/22)
A series of novel 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives was designed, and synthesized based on our previous studies. Also their activities were evaluated as competitive inhibitors of protein tyrosine phosphatase 1B (PTP1B). Compounds 6d-6g, 7b, 7c, 7e, 7j, 7k, 7m, 14b and 14e-14f showed potent inhibitory effects against PTP1B, and compound 7e, the most potent among the series, had an IC50 of 4.6 μM. Also a Surflex-Dock docking model of 7e was studied. Compound 7e showed a negative binding energy of -7.35 kcal/mol and a high affinity to PTP1B residues (Gly220, Ala217, Arg221, Asp181, Ser216, Cys215, Phe182, Gln262 and Ile219) in the active sites, indicating that it may stabilize the open form and generate tighter binding to the catalytic sites of PTP1B.
Facile synthesis of diarylmethanes via quinone methides
Tangdenpaisal, Kassrin,Phakhodee, Wong,Ruchirawat, Somsak,Ploypradith, Poonsakdi
, p. 933 - 941 (2013/07/25)
A novel acid-mediated generation of quinone methides followed by nucleophilic addition of electronrich aromatic compounds to furnish diarylmethanes has been developed. A wide range of electronrich aromatic compounds including some heterocycles can be employed for this reaction to provide the corresponding diarylmethanes in good yields and regioselectivities.
Design, synthesis, and biological activity of potent and orally available g protein-coupled receptor 40 agonists
Sasaki, Shinobu,Kitamura, Shuji,Negoro, Nobuyuki,Suzuki, Masami,Tsujihata, Yoshiyuki,Suzuki, Nobuhiro,Santou, Takashi,Kanzaki, Naoyuki,Harada, Masataka,Tanaka, Yasuhiro,Kobayashi, Makoto,Tada, Norio,Funami, Miyuki,Tanaka, Toshimasa,Yamamoto, Yoshio,Fukatsu, Kohji,Yasuma, Tsuneo,Momose, Yu
experimental part, p. 1365 - 1378 (2011/05/05)
G protein-coupled receptor 40 (GPR40) is being recently considered to be a new potential drug target for the treatment of type 2 diabetes because of its role in the enhancement of free fatty acid-regulated glucose-stimulated insulin secretion in pancreatic β-cells. We initially identified benzyloxyphenylpropanoic acid (1b) (EC50 = 510 nM), which was designed based on the structure of free fatty acids, as a promising lead compound with GPR40 agonist activity. Chemical modification of compound 1b led to the discovery of 3-{4-[(2′,6′-dimethylbiphenyl-3-yl)methoxy]-2- fluorophenyl}propanoic acid (4p) as a potent GPR40 agonist (EC50 = 5.7 nM). Compound 4p exhibited acceptable pharmacokinetic profiles and significant glucose-lowering effects during an oral glucose tolerance test in diabetic rats. Moreover, no hypoglycemic event was observed even after administration of a high dose of compound 4p to normal fasted rats. These pharmacological results suggest that GPR40 agonists might be novel glucose-dependent insulin secretagogues with little or no risk of hypoglycemia.
Synthesis and Insecticidal Activity of Lignan Analogs (II)
Yamauchi, Satoshi,Taniguchi, Eiji
, p. 412 - 417 (2007/10/02)
The influence of the 6-methoxy-2-methoxymethyl-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl group on the insecticidal activity of haedoxans was studied by synthesizing an analog without the (methoxymethyl)methinoxy moiety of the benzodioxanyl group t
