80776-66-5Relevant academic research and scientific papers
Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family
Afanasyev, Oleg I.,Podyacheva, Evgeniya,Rudenko, Alexander,Tsygankov, Alexey A.,Makarova, Maria,Chusov, Denis
, p. 9347 - 9360 (2020/08/14)
A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.
Novel PDE5 inhibitors derived from rutaecarpine for the treatment of Alzheimer's disease
Dong, Yan-Hua,Huang, Xian-Feng,Ke, Heng-Ming,Song, Guo-Qiang,Wang, Jin-Hui,Xu, De-Feng
supporting information, (2020/03/23)
A series of novel rutaecarpine derivatives were synthesized and subjected to pharmacological evaluation as PDE5 inhibitors. The structure–activity relationships were discussed and their binding conformation and simultaneous interaction mode were further clarified by the molecular docking studies. Among the 25 analogues, compound 8i exhibited most potent PDE5 inhibition with IC50 values about 0.086 μM. Moreover, it also produced good effects against scopolamine-induced cognitive impairment in vivo. These results might bring significant instruction for further development of potential PDE5 inhibitors derived from rutaecarpine as a good candidate drug for the treatment of Alzheimer's disease.
New topoisomerases inhibitors: Synthesis of rutaecarpine derivatives and their inhibitory activity against topoisomerases
Kim, Seung Ill,Lee, Seung Ho,Lee, Eung-Seok,Lee, Chong-Soon,Jahng, Yurngdong
, p. 785 - 789 (2012/08/29)
A series of rutaecarpine derivatives were prepared by employing previously reported methods and their inhibitory activities against topoisomerase I and II were evaluated. Among them, strongly cytotoxic 10-bromorutaecarpine and 3-chlororutaecarpine showed strong inhibitory activities against topo I and II.
Efficient syntheses of 2,3-disubstituted natural quinazolinones via iridium catalysis
Fang, Jie,Zhou, Jianguang
, p. 2389 - 2391 (2012/04/11)
Natural products sclerotigenin, pegamine, deoxyvasicinone, mackinazolinone, and rutaecarpine were synthesized. Core quinazolinone structures were constructed via Ir catalysis. The Royal Society of Chemistry 2012.
Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1)
Chen, Zhuo,Hu, Gaoyun,Li, Dai,Chen, Jun,Li, Yuanjian,Zhou, Huayong,Xie, Ye
experimental part, p. 2351 - 2359 (2009/09/08)
Rutaecarpine is the major alkaloid component of Wu-Chu-Yu, a well known Chinese herbal drug. It has been reported that rutaecarpine causes the vasodilator, hypotensive effects by stimulation of CGRP synthesis and release via activation of TRPV1. In present study, 23 rutaecarpine analogues were designed and synthesized. Then, the vasodilator effects of theses compounds were screened by rat aortic ring experiment. The result showed that the 14-N atom of rutaecarpine might be the key site for the activity. The 5-carbonyl might make lower contribution to the effect. And simple substitute in indole-ring or quinazoline-ring would not enhance the vasodilator effect unless in proper position with proper group. One of these compounds, 10-methylrutaecarpine, exhibited similar effect with rutaecarpine. Further functional experiments showed its vasodilator and hypotensive effect were related to the stimulation of CGRP release via activation of TRPV1. The vasodilator effects of these compounds were evaluated and the structure-activity relationship was elucidated for the first time. The results suggested a new direction of valuable TRPV1 agonist as anti-hypertensive drugs.
A facile total synthesis of rutaecarpine
Chavan, Subhash P.,Sivappa
, p. 997 - 999 (2007/10/03)
The indoloquinazoline alkaloid rutaecarpine has been synthesized efficiently by employing 9,10,11,12-tetrahydro-4H-pyrido[2,1-b]quinazoline-4,9- dione (4) as a key intermediate, which was prepared by adapting a Dieckmann condensation-decarboxylation sequence from quinazolinone diester 6.
Facile zeolite induced Fischer-indole synthesis: A new approach to bioactive natural product rutaecarpine
Mhaske, Santosh B.,Argade, Narshinha P.
, p. 3417 - 3420 (2007/10/03)
Starting from glutaric anhydride (5) we have demonstrated an elegant six-step practical synthesis of bioactive natural product rutaecarpine (1a) via o-amidoglutaranilic acid formation, esterification, chemoselective ester reduction, intramolecular dehydrative cyclizations, hydrazone formation and zeolite induced Fischer-indole synthesis with 53% overall yield. The conditions employed in the present synthesis are mild, efficient and general.
A simple synthesis of rutaecarpine
Lee, Seung Ho,Kim, Seung Ill,Park, Jae Gyu,Lee, Eung Seok,Jahng, Yurngdong
, p. 1555 - 1567 (2007/10/03)
Indoloquinazoline alkaloid rutaecarpine was efficiently synthesized by employing 9,10,11,12-tetrahydro-4H-pyrido[2,1-b]quinazoline-4,9-dione as a key intermediate, whose 9-carbonyl group was introduced by benzylidene formation, followed by ozonolysis.
Indolo[2',3';3,4]pyrido[2,1-b]quinazoline-5-ones, a process for the preparation thereof, and diuretic compositions and methods using them
-
, (2008/06/13)
New Rutecarpine analogs are disclosed having Rutecarpine-like activity, especially diuretic activity. Also a novel process for the preparation of the Rutecarpine analogs is disclosed.
Nitrogen Bridgehead Compounds. Part 45. Synthesis of 6-Arylhydrazono-6,7,8,9-tetrahydro-11H-pyridoquinazolin-11-ones
Koekoesi, Jozsef,Hermecz, Istvan,Podanyi, Benjamin,Szasz, Gyoergy,Meszaros, Zoltan
, p. 1301 - 1306 (2007/10/02)
A series of 6-arylhydrazono-6,7,8,9-tetrahydro-11H-pyridoquinazolin-11-ones 3-37, convenient starting materials for indolopyridoquinazolines, were prepared by diazonium coupling between aryldiazonium chlorides and 6,7,8,9-tetrahydro- 2, 6-formyl-6,7,8,9-tetrahydro- 39, 6-(dimethylamino)methylene-6,7,8,9- 38 or 6-carboxyl-6,7,8,9-tetrahydro-11H-pyridoquinazolin-11-ones 43.The arylhydrazono derivatives were also prepared from 6-bromo- 45 or 6,6-dibromo-6,7,8,9-tetrahydro-11H-pyridoquinazolines 46 with arylhydrazines.The structures of the 6-arylhydrazonopyridoquinazolines were characterized by uv and 1H nmr spectroscopy.The 6-arylhydrazono derivatives show a solvent-dependent E-Z isomerism.
