6412-87-9Relevant articles and documents
A metal-free method for the facile synthesis of indanonesviathe intramolecular hydroacylation of 2-vinylbenzaldehyde
He, Guoxue,Ma, Jinyu,Zhou, Jianhui,Li, Chunpu,Liu, Hong,Zhou, Yu
supporting information, p. 1036 - 1040 (2021/02/09)
A facile method for the synthesis of indanones was developed under metal- and additive-free conditions, whereinl-proline served as an efficient and environmentally benign catalyst. Compared with previously synthesized indanones, synthesis by the transition-metal-catalyzed intramolecular hydroacylation of 2-vinylbenzaldehyde provided a more green synthetic pathway to indanone scaffolds with good to excellent yields. More importantly, it could be used to synthsize the anti-AD drug donepezil.
First total synthesis of Papilistatin
Wu, Meng,Li, Ling,Feng, An-Zheng,Su, Bo,Liang, De-Min,Liu, Yu-Xiu,Wang, Qing-Min
experimental part, p. 2539 - 2542 (2011/05/06)
Papilistatin has been isolated recently and found to have good anticancer and antibacterial activity. Papilistatin is a unique phenanthrene-1,10- dicarboxylic acid. The first total synthesis of papilistatin is described here with radical cyclisation as the key step.
Design and synthesis of brazilin-like compounds
Pan, Chengxue,Zeng, Xianghui,Guan, Yifu,Jiang, Xiangliu,Li, Liang,Zhang, Hongbin
supporting information; experimental part, p. 425 - 429 (2011/04/22)
A general and flexible synthetic route, which leads to the synthesis of brazilin-like compounds, was developed. The aza-brazilin derivatives show strong anticancer activities in MTT assay towards a number of human cancer cell lines including HT29, A549, HL60, and K562. Georg Thieme Verlag Stuttgart New York.
Ruthenium-catalyzed cyclization of 2-alkyl-1-ethynylbenzenes via a 1,5-hydrogen shift of ruthenium-vinylidene intermediates
Odedra, Arjan,Datta, Swarup,Liu, Rai-Shung
, p. 3289 - 3292 (2008/02/03)
(Chemical Equation Presented) Catalytic cyclization of 2-alkyl-1- ethynylbenzene derivatives was implemented by TpRuPPh3(CH 3CN)2PF6 (10 mol %) in hot toluene (105 °C, 36-100 h) to form 1-substituted-1H-indene and 1-indanone products; such cyclizations proceeded more efficiently for substrates bearing electron-rich benzenes. We propose that the cyclization mechanism involves a 1,5-hydrogen shift of initial metal-vinylidene intermediate.
Microwave-enhanced carbonylative generation of indanones and 3-acylaminoindanones
Wu, Xiongyu,Nilsson, Peter,Larhed, Mats
, p. 346 - 349 (2007/10/03)
(Chemical Equation Presented). The development of microwave-accelerated protocols for palladium(0)-catalyzed carbonylative cyclization of unsaturated aryl bromides and chlorides is described. By employing o-bromostyryl derivatives lacking substituents on the vinylic bond, molybdenum hexacarbonyl-mediated in situ carbonylation delivered a set of indan-1-one products in high yield after only 20 min of heating. Without the addition of the tri-tert-butylphosphine releasing Fu-salt ((t-Bu)3PHBF4), only incomplete conversions of sluggish o-styryl bromides and chlorides were realized. Internal and chemoselective palladium(0)-catalyzed Heck arylations of enamides afforded suitable starting materials for subsequent rapid ring-closing reactions. Microwave-heated intramolecular in situ carbonylation of these electron-rich and sterically congested olefins conveniently afforded eight functionalized 3-acylaminoindanone derivatives in a novel synthetic process. Attempted carbonylative annulation of electron-poor o-bromocinnamic acid derivatives furnished only the corresponding lactones via a competing hydroxycarbonylation- Michael addition reaction sequence.
Nonneurotoxic Tetralin and Indian Analogues of 3,4-(Methylenedioxy)amphetamine (MDA)
Nichols, David E.,Brewster, William K.,Johnson, Michael P.,Oberlender, Robert,Riggs, Robert M.
, p. 703 - 710 (2007/10/02)
Four cyclic analgues of the psychoactive phenethylamine derivative 3,4-(methylenedioxy)amphetamine were studied.These congeners, 5,6- and 4,5-(methylenedioxy)-2-aminoindan (3a and 4a, respectively), and 6,7- and 5,6-(methylenedioxy)-2-aminotetralin (3b and 4b, respectively) were tested for stimulus generalization in the two-lever drug-discrimination paradigm.Two groups of rats were trained to discriminate either LSD tartrate (0.08 mg/kg) from saline, or (+/-)-MDMA*HCl (1.75 mg/kg) from saline.In addition, a 2-aminoindan (5a) and 2-aminotetralin (5b) congener of the hallucinogenic amphetamine 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) were also evaluated.None of the methylenedioxy compounds substituted in LSD-trained rats, while both 3a and 3b fully substituted in MDMA-trained rats.Compounds 4a and 4b did not substitute in MDMA-trained rats.Compounds 5a and 5b did not substitute in MDMA-trained rats, although 5a substituted in LSD-trained rats, but with relatively low potency compared to its open-chain counterpart.In view of the now well-established serotonin neurotoxicity of 3,4-(methylenedioxy)amphetamine and its N-methyl homologue 1, 3a and 3b were evaluated and compared to 1 for similar toxic effects following a single acute dose of 40 mg/kg sc.Sacrifice at 1 week showed that neither 3a nor 3b depressed rat cortical or hippocampal 5-HT or 5-HIAA levels nor were the number of binding sites (Bmax) depressed for paroxetine.By contrast, and in agreement with other reports, 1 significantly depressed all three indices of neurotoxicity.These results indicate that 3a and 3b have acute behavioral pharmacology similar to 1 but that they lack similar serotonin neurotoxicity.
