- Synthesis of 1-aryltetrahydroisoquinoline alkaloids and their analogs
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Three alkaloids of the cryptostylin series and 20 monomolecular and 3 bimolecular 1-aryltetrahydroisoquinoline derivatives were prepared using the Picte-Spengler reaction.
- Zhurakulov,Vinogradova,Levkovich
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- Synthesis of isoquinoline alkaloids via oxidative amidation-bischler- napieralski reaction
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A straightforward synthesis of -keto amides by coupling primary amines with aryl dibromoethanones under oxidative amidation conditions has been developed. The -keto amides were then subjected to heterocyclodehydration reaction under Bischler-Napieralski conditions followed by aromatization with DBU provided 1-benzoyl isoquinolines in a two-stage process. Utilizing this methodology, isoquinoline alkaloids such as thalmicrinone, papavaraldine, and pulcheotine A were synthesized in excellent yields. Georg Thieme Verlag Stuttgart · New York.
- Shankar,More, Satish S.,Madhubabu,Vembu,Syam Kumar
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supporting information; experimental part
p. 1013 - 1020
(2012/06/01)
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- Synthesis and biological evaluation of berberine analogues as novel up-regulators for both low-density-lipoprotein receptor and insulin receptor
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Berberine (BBR) is a natural compound with up-regulating activity on both low-density-lipoprotein receptor (LDLR) and insulin receptor (InsR). This one-drug-multiple-target characteristic might be suitable for the treatment of metabolic syndrome. In searching for up-regulators effective for both LDLR and InsR expression, the structure-activity relationship (SAR) analysis for BBR analogues was done. Fourteen BBR analogues were designed, synthesized and biologically evaluated. SAR analysis revealed that appropriate modifications on the phenyl ring A or D of BBR might retain the up-regulatory activities on the expression of both LDLR and InsR. Among these compounds, compound 13a bearing 9-methoxy and 10-hydroxyl on the ring D showed promising activities on either LDLR or InsR gene expression. The 10-hydroxyl of 13a could be an arm to connect proper chemical groups for optimizing drug-bioavailability in vivo. Thus, 13a could be considered to be a parent compound to make pro-drugs for either blood lipids or glucose.
- Wang, Yan-Xiang,Wang, Yu-Ping,Zhang, Hao,Kong, Wei-Jia,Li, Ying-Hong,Liu, Fei,Gao, Rong-Mei,Liu, Ting,Jiang, Jian-Dong,Song, Dan-Qing
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scheme or table
p. 6004 - 6008
(2010/06/16)
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- Glycosylation-induced asymmetric synthesis of 1-substituted tetrahydroisoquinolines
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Activation of imines by N-glycosylation and simultaneous diastereodifferentiation in reactions of the formed N-glycosyl iminium ions provide new stereoselective routes to 1-substituted tetrahydroisoquinolines. Pictet-Spengler reactions induced by N-galact
- Allef, Petra,Kunz, Horst
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p. 421 - 436
(2008/09/17)
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- Berberis ALKALOIDS. XXII. INTEBRININE AND INTEBRIMINE - NEW ALKALOIDS FROM Berberis integerrima
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The known alkaloids reticuline, isoboldine, isocorydine, glaucine, armepavine, oxyacanthine, and heliamine and the new alkaloids intebrinine and intebrimine have been isolated from the total alkaloids of the leaves of Berberis integerrima, and structures
- Karimov, A.,Vinogradova, V. I.,Shakirov, R.
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- SYNTHESIS BASED ON &β-PHENYLETHYLAMINES. IV. SYNTHESIS AND ANTIARRHYTHMIC ACTIVITY OF SUBSTITUTED PHENYLALKYLAMINES AND N-BENZYLTETRAHYDROISOQUINOLINES
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A number of N-benzyltetrahydroisoquinolines forming analogues of sendaverine have been synthesized.Results on the pharmacological activity of the compounds synthesized are presented.
- Vinogradova, V. I.,Golodnyuk, T. I.,Tulyaganov, N.,Yunusov, M. S.,Baratov, N. Yu.
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p. 341 - 345
(2007/10/02)
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- Ruthenium dioxide in fluoro acid medium. III. Aplication to the synthesis of aporphinic, homoaporphinic and dibenzazocinic alkaloids. Studies towards the preparation of azafluoranthenic skeleton
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Intramolecular oxidative couplings of phenylalkyltetrahydroisoquinoline precursors in aporphinic and homoaporphinic alkaloids by using RuO2,2H2O in fluoro acidic media were performed. A comparative study of our reagent with TTFA has been made with different precursors. The procedure was also extended to the synthesis of one dibenzazocinic alkaloid. Then, we attempted to synthetize the azafluoranthenic ring, using phenolic and non phenolic isoquinoline precursors.
- Landais,Robin
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p. 7185 - 7196
(2007/10/02)
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