221348-93-2Relevant academic research and scientific papers
An organocatalyst from renewable materials for the synthesis of coumarins and chromenes: Three-component reaction and multigram scale synthesis
Sangsuwan, Rapeepat,Sangher, Sasithorn,Aree, Thammarat,Mahidol, Chulabhorn,Ruchirawat, Somsak,Kittakoop, Prasat
, p. 13708 - 13718 (2014)
A new concept of catalysts which are prepared from renewable materials is demonstrated. It is known that amino acids (e.g., proline and hydroxyproline) are robust organocatalysts for several reactions. Bovine tendons which are proteins rich in hydroxyproline and proline were used as a source of amino acids. An acid hydrolysate of tendons (a TH catalyst) could catalyze two reactions: (i) the synthesis of coumarins and chromenes under solvent-free conditions and (ii) the synthesis of densely functionalized 4H-chromenes via a three-component reaction. Moreover, an economical and easily accessible TH catalyst is applicable in a multigram scale synthesis of coumarins and chromenes, as well as in the three-component reaction for chromene synthesis. A catalytic activity of hydroxyproline for the synthesis of 4H-chromenes via the three-component reaction was also discovered. The present work demonstrates not only the green catalysts from renewable materials, but also an environmentally benign preparation of coumarins and chromenes. This journal is the Partner Organisations 2014.
Synthesis, spectroscopic and photophysical studies of xanthene derivatives
Taghartapeh, Mohammad Ramezani,Noroozi Pesyan, Nader,Rashidnejad, Hamid,Khavasi, Hamid Reza,Soltani, Alireza
, p. 862 - 873 (2017/08/29)
We report on the experimental, crystal structure and computational investigation of a new class of xanthenes obtained by the reaction of salicylaldehyde and its derivatives with, 5,5-Dimethylcyclohexane-1,3-dione (Dimedone). The synthesized xanthenes were
Diethylamine-catalyzed environmentally benign synthesis of 1-oxo-hexahydroxanthenes and bis-coumarins at ambient temperature
Kupwade, Ravindra V.,Pandit, Kapil S.,Desai, Uday V.,Kulkarni, Makarand A.,Wadgaonkar, Prakash P.
, p. 6313 - 6325 (2016/07/06)
Abstract: An extremely simple, economical and environmentally benign protocol has been described for one-pot synthesis of 1-oxo-hexahydroxanthenes by pseudo three-component condensation between salicylaldehydes and dimedone, cyclohexane-1,3-dione or 5-met
A rapid and efficient CsF catalyzed tandem Knoevenagel-Michael reaction
Khan, Khalid Mohammed,Khan, Imran,Perveen, Shahnaz,Malik, Muhammad Imran
, p. 1 - 5 (2014/01/06)
A simple, experimentally rapid and efficient CsF catalyzed tandem Knoevenagel-Michael reaction protocol is developed for the synthesis of a series of functionalized 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl- 2,3,4,9-tetrahydro-1H-xanthe
Catalytic performance of heteropolyacids as efficient and eco-friendly catalysts for the one-pot synthesis of benzopyran derivatives
Zakeri, Masoumeh,Heravi, Majid M.,Oskooie, Hossein A.,Bamoharram, Fatemeh F.
experimental part, p. 916 - 921 (2011/02/27)
An efficient and improved procedure for the synthesis of benzopyran derivatives has been achieved with Keggin-type and Preyssler-type heteropolyacids (HPA) catalysts in one-pot reaction under solvent-free conditions. Copyright Taylor & Francis Group, LLC.
(9S)-9-(2-Hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-2,3,4, 9-tetrahydro-1H-xanthen-1-one, a selective and orally active neuropeptide Y Y5 receptor antagonist
Sato, Nagaaki,Jitsuoka, Makoto,Shibata, Takunobu,Hirohashi, Tomoko,Nonoshita, Katsumasa,Moriya, Minoru,Haga, Yuji,Sakuraba, Aya,Ando, Makoto,Ohe, Tomoyuki,Iwaasa, Hisashi,Gomori, Akira,Ishihara, Akane,Kanatani, Akio,Fukami, Takehiro
experimental part, p. 4765 - 4770 (2009/07/19)
(9S)-9-(2-Hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-2,3,4, 9-tetrahydro-1H-xanthen-1-one ((S)-1) was identified as a selective and orally active neuropeptide Y Y5 receptor antagonist. The structure-activity relationship for this structural class was investigated and showed that limited substitution on the phenyl ring was tolerated and that modification of the 4,4-dimethyl group of the cyclohexenone and the 3,3-dimethyl group of the xanthenone parts slightly improved potency. The plasma concentration-time profile after oral administration of (S)-1 in Sprague-Dawley (SD) rats showed significant in vivo racemization of (S)-1 and that (S)-1 is cleared much more quickly than (R)-1. The duration of (S)-1 in SD rats after oral administration of (RS)-1 racemate was twice as long as that following oral administration of (S)-1. The Cmax values of (S)-1 after administration of (S)-1 and (RS)-1 were comparable, and the brain to plasma ratio for (S)-1 was 0.34 in SD rats. In our acute D-Trp34NPY-induced food intake model, both (S)-1 and (RS)-1 showed potent and dose-dependent efficacy. Therefore, the use of (RS)-1 is suitable for studies that require sustained plasma exposure of (S)-1.
