- Structure-activity relationships of quaternary protoberberine alkaloids having an antimalarial activity
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Seventeen quaternary protoberberine alkaloids related to berberine 1 were tested for antimalarial activity in vitro against Plasmodium falciparum and structure-activity relationships are proposed. The activity of the protoberberine alkaloids was influenced by the type of the oxygen substituents on rings A, C and D and the position of the oxygen functions on ring D. The position of the oxygen functions on ring D and the type of the oxygen substituents at the C-13 position (ring C) strongly influenced the activity. Shifting the oxygen functions at C-9 and C-10 to C-10 and C-11 on ring D resulted in a significant increase in the activity. Compounds bearing a methylenedioxy function at C-2 and C-3 (ring A) or C-9 and C-10 (ring D) showed higher activity than those which have methoxy groups at the same positions. Introduction of a methoxy group into the C-1 position (ring A) decreased the activity. Replacement of a hydroxy group at C-2 or C-3 (ring A) by a methoxy group led to a reduction in the activity. Displacement of a hydroxy function at C-13 (ring C) by the oxygen substituents such as OMe, OEt, OCOOEt, and OCON(Me)2 reduced the activity. In the same replacement at C-9 (ring D), the activity depended upon the type of the oxygen function. Six protoberberines displayed more potent activity than berberine 1. The activity decreased in the order: 10, 11, 17 and 18 > 7 and 8 > 1.
- Iwasa, Kinuko,Nishiyama, Yumi,Ichimaru, Momoyo,Moriyasu, Masataka,Kim, Hye-Sook,Wataya, Yusuke,Yamori, Takao,Takashi, Turuo,Lee, Dong-Ung
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- Method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control
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The invention discloses a method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control. The method comprises the following steps: improving a substituent group of a high-iodine salt leaving group, generating pyridine alkyne under the action of relatively mild potassium tert-butoxide, and carrying out [4 + 2] cycloaddition reaction on the pyridine alkyne and diene to obtain polysubstituted isoquinoline ring precursor compounds. Ring opening and aromatization of the isoquinoline ring precursor are realized by developing a novel iridium-catalyzed cross-coupling method, polysubstituted isoquinoline ring compounds with connecting capacity are efficiently synthesized, and then the polysubstituted isoquinoline ring compounds are coupled with a high-activity polysubstituted cyclic boric acid to obtain 3-aryl isoquinoline high-grade intermediates. Through application of two different chemical principles, regulation and control of the 3-aryl isoquinoline high-grade intermediates are realized, and benzophenanthridine and protoberberine alkaloids are modularly, diversely and efficiently synthesized.
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- Four proto compound in the preparation of anti-depression drug application
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The invention discloses application of tetrahydroproberberine compounds to prepare antidepressants. Experiments confirm that tetrahydroproberberine compounds are capable of effectively shortening the swimming motionless time of a depression-model mouse, obviously shortening the tail suspending accumulative motionless time of a depression-model mouse and obviously improving the depression state caused by reserpine of a mouse, and show certain anti-depression effect.
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Paragraph 0063-0065
(2017/08/25)
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- Palmatine derivatives and application thereof to preparation of anti-alzheimer-disease medicament
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The invention discloses a series of derivatives prepared by extracting from Fibraurea recisa Pierre. and carrying out separation and purification to obtain palmatine, using the palmatine as a lead compound, and performing corresponding chemical reactions.
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Paragraph 0044; 0045
(2016/10/09)
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- Compounds and Compositions for Modulating Lipid Levels and Methods of Preparing Same
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The present technology relates to compounds of Formulas I-VI and methods of making and using such compounds. Methods of use include prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Compounds disclosed herein also increase HDL-C, lower total cholesterol, LDL-cholesterol, and triglycerides and increase hepatic LDL receptor expression, inhibit PCSK9 expression, and activate AMP-activated protein kinase.
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Page/Page column 70
(2011/02/15)
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