- Semi-synthesis and Structure–Activity Relationship of Neuritogenic Oleanene Derivatives
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(3S,4R)-23,28-Dihydroxyolean-12-en-3-yl (2E)-3-(3,4-dihydroxyphenyl)acrylate (1 a), which possesses significant neuritogenic activity, was isolated from the traditional Chinese medicine (TCM) plant, Desmodium sambuense. To confirm the structure and to assess biological activity, we semi-synthesized 1 a from commercially available oleanolic acid. A series of novel 1 a derivatives was then designed and synthesized for a structure–activity relationship (SAR) study. All synthetic derivatives were characterized by analysis of spectral data, and their neuritogenic activities were evaluated in assays with PC12 cells. The SAR results indicate that the number and position of the hydroxy groups on the phenyl ring and the triterpene moiety, as well as the length of the (saturated or unsaturated) alkyl chain that links the phenyl ring with the triterpene critically influence neuritogenic activity. Among all the tested compounds, 1 e [(3S,4R)-23,28-dihydroxyolean-12-en-3-yl (2E)-3-(3,4,5-trihydroxyphenyl)acrylate] was found to be the most potent, inducing significant neurite outgrowth at 1 μm.
- Bian, Linglin,Cao, Shining,Cheng, Lihong,Nakazaki, Atsuo,Nishikawa, Toshio,Qi, Jianhua
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supporting information
p. 1972 - 1977
(2018/09/06)
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- PARA-QUINOL DERIVATIVES AND METHODS OF STEREO SELECTIVELY SYNTHESIZING AND USING SAME
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This application relates to para-quinol derivatives, such as analogues of manumycins, aranorosins and gymnastatins. This application also relates to methods of synthesizing and using the para-quinol derivatives. In one embodiment of the invention a compou
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Page/Page column 24-25
(2010/11/30)
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- Nitration of cinnamic acids using cerium (IV) ammonium nitrate immobilized on silica
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Treatment of cinnamic acids with cerium (IV) ammonium nitrate supported on silica (CAN/SiO2) was used to synthesize nitro derivative and ipso substitution products. The position of the substituents defines the type and the yields of the product
- Messere, Anna,Gentili, Alessandra,Garella, Isidoro,Temussi, Fabio,Di Blasio, Benedetto,Fiorentino, Antonio
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p. 3317 - 3324
(2007/10/03)
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- Benzene derivatives having NGF production-promoting activity
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A compound of the formula (I): STR1 wherein R1 is an unsubstituted or substituted amino group, a protected amino group, or a nitro group; R2 is an unsubstituted or substituted amino group, a protected amino group, an unsubstituted or substituted hydroxy group or a protected hydroxy group; R3 is an unsubstituted or substituted amino group, m is 0 to 2; n is 0 to 6; with the proviso that when m is 0, then n is an integer from 2 to 6, and pharmaceutically acceptable salts thereof. Compounds of formula (I) except those wherein R1 is a nitro group have activity in promoting the production of nerve growth factor.
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