- Partial synthesis of 14-deoxy-14-aminotriptolide
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Triptolide is a diterpene triepoxide isolated from Tripterygium wilfordii, a Chinese medicinal plant and possessing a wealth of biological activities. In order to produce more soluble derivatives of triptolide, its 14-amino analogue was prepared. Initial attempts at its preparation using classical displacements led to rearranged compounds and success was finally met using carefully controlled Borch conditions. 14-Deoxy-14-aminotriptolide was thus prepared for the first time and it was found 10 times less cytotoxic than the parent compound.
- Kaloun, El Bachir,Long, Christophe,Molinier, Nicolas,Brel, Viviane,Cantagrel, Frédéric,Massiot, Georges
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p. 1895 - 1898
(2016/04/19)
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- Semisynthesis of triptolide analogues: Effect of B-ring substituents on cytotoxic activities
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A series of B-ring modified analogues of triptolide were synthesized and tested for their cytotoxicity against two human tumor cell lines (U251 and PC-3). From the current investigation, the structure-cytotoxic activity relationships of these analogues su
- Xu, Hongtao,Chen, Yi,Tang, Huanyu,Feng, Huijin,Li, Yuanchao
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p. 5671 - 5674
(2015/01/08)
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- Semisynthesis of triptolide analogues: Effect of γ-lactone and C-14 substituents on cytotoxic activities
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Triptolide γ-lactone and C-14 analogues were prepared and evaluated cytotoxity against human lung adenocarcinoma epithelial A549 cells and human colon adenocarcinoma HT-29 cells. γ-Lactone substructure and C-14 substituents affected the biological activities significantly.
- Aoyagi, Yutaka,Hitotsuyanagi, Yukio,Hasuda, Tomoyo,Fukaya, Haruhiko,Takeya, Koichi,Aiyama, Ritsuo,Matsuzaki, Takeshi,Hashimoto, Shusuke
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scheme or table
p. 3046 - 3049
(2011/06/26)
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- Efficient syntheis of the key intermediate triptophenolide methyl ether for the synthesis of(-)-triptolide
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An efficient synthesis of triptophenolide methyl ether 4 from the readily available abietic acid 3 in nine steps is described and successfully applied to the synthesis of (-)-triptolide 1.The route is of characteristic of low cost, high yield and easy operation.In addition, every reaction in this route has been successfully scaled-up to a 100 g substrate level without loss of yield.
- Zhou, Bing,Li, Xiaomei,Feng, Huijin,Li, Yuanchao
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scheme or table
p. 5396 - 5401
(2010/08/19)
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- TRIPTOLIDE PRODRUGS
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The invention provides compounds of formula (I): or a salt thereof. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods using the compounds of formula I.
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Page/Page column 28-29
(2010/11/18)
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- Semisynthesis of C-ring modified triptolide analogues and their cytotoxic activities
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Several C-ring modified analogues of a potent antileukemic diterpene, triptolide (1), were synthesized and their structure-activity relationships were studied.
- Aoyagi, Yutaka,Hitotsuyanagi, Yukio,Hasuda, Tomoyo,Fukaya, Haruhiko,Takeya, Koichi,Aiyama, Ritsuo,Matsuzaki, Takeshi,Hashimoto, Shusuke
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p. 1947 - 1949
(2007/10/03)
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- Cytotoxic Biotransformed Products from Triptonide by Aspergillus niger
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The diterpenoid triepoxides are the major active constituents of Tripterygium wilfordii with potent antitumor and immune activities. But the strong toxicity of these compounds has restricted their application to a great extent. In order to find more effective compounds with less toxicity, structural modifications of triptonide (1) by Aspergillus niger (AS 3.739) were investigated and four biotransformed products were obtained. Based on their chemical and spectral data, their structures were elucidated as 5α-hydroxytriptonide (2), triptolide (3), 17-hydroxytriptonide (4), and 16-hydroxytriptonide (5), among which 2, 4 and 5 are new compounds. All the three new transformed products showed cytotoxic activities against the majority of the human tumor cell lines tested, however, they are found to possess less cytotoxic activity when compared with 1. Both compounds 4 and 5 showed similar cytotoxic activity and their IC50 values were 5-15 fold less than 1, while 2 is about 100 times less active than 1.
- Ning, Lili,Qu, Guiqin,Ye, Min,Guo, Hongzhu,Bi, Kaishun,Guo, Dean
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p. 804 - 808
(2007/10/03)
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- Enantioselective Total Synthesis of (-)-Triptolide, (-)-Triptonide, (+)-Triptophenolide, and (+)-Triptoquinonide
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The first enantioselective total synthesis of (-)-triptolide (1), (-)-triptonide (2), (+)-triptophenolide (3), and (+)-triptoquinonide (4) was completed. The key step involves lanthanide triflate-catalyzed oxidative radical cyclization of (+)-8-phenylmenthyl ester 30 mediated by Mn(OAc)9, providing intermediate 31 with good chemical yield (77%) and excellent diastereoselectivity (dr 38:1). (+)-Triptophenolide methyl ether (5) was then prepared in >99% enantiomeric excess (>99% ee), and readily converted to natural products 1-4. In addition, transition state models were proposed to explain the opposite chiral induction observed in the oxidative radical cyclization reactions of chiral β-keto esters 17 (without an α-substituent) and 17a (with an α-chloro substituent).
- Yang, Dan,Ye, Xiang-Yang,Xu, Ming
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p. 2208 - 2217
(2007/10/03)
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- Immunosuppressive compounds and methods
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Compounds and methods for use in immunosuppressive and anti-inflammatory treatment are described. The compounds are triptolide analogs with improved water solubility and low toxicity.
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