秦勇
个性化签名
- 姓名:秦勇
- 目前身份:
- 担任导师情况:
- 学位:
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学术头衔:
博士生导师, 教育部“新世纪优秀人才支持计划”入选者
- 职称:-
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学科领域:
药物化学
- 研究兴趣:
秦勇博士于1989年在云南大学化学系获理学学士学位;1995年5月于中科院化学研究所获理学博士学位;1995年6月至1996年8月,在中科院成都有机化学研究所任助理研究员,副研究员;1996年8月至2000年8月,美国佛蒙特大学化学系博士后;2000年9月至2002年9月,美国圣地亚哥高技术生物制药公司Triad Therapeutics Inc.研究员;2003年3月至今,四川大学华西药学院教授,博士生导师,四川省杰出青年基金和教育部新世纪优秀人才支持计划入选者,四川省卫生厅学术技术带头人。2002年获四川省科学技术进步一等奖,2005年获四川省青年科技奖。目前为四川大学华西药学院副院长。
秦勇博士的科学研究活动共可分为四个阶段。第一阶段研究(1989-1996)从事手性噁唑硼烷、手性亚砜诱导的环加成反应和手性氮膦一氧膦配体催化的不对称反应研究。第二阶段研究(1996-2000)从事具有抗癌活性吲哚类生物碱的全合成和构效关系的研究,在这期间独立完成两个结构复杂的吲哚类生物碱16a’-homovinblastine和16a’-homoleurosidine的全合成,它们是分别通过25步和21步反应制备的。通过该目标分子的成功合成,验证了溶液的pH值可调控长春花碱类似物的有效活性构象,为进一步设计和合成能在肿瘤部位活化的靶向抗肿瘤前药提供了直接的实验证据,这些研究工作是一些高难度和极具挑战性的工作。第三阶段研究活动(2000-2003)为在美国圣地亚哥高科技生物制药公司Triad Therapeutics Inc.从事以激酶作为药物作用目标酶的新药研究工作,在核磁共振技术的帮助下,设计和合成与风湿性关节炎相关的激酶p38抑制剂,这些工作获得三项美国发明专利授权。第四阶段在四川大学华西药学院从事与天然产物相关的创新药物和化学生物学的研究,开展具有抗癌活性的吲哚生物碱的全合成及构效关系研究,并以作用机制明确的生物碱为先导化合物,结合生物信息最新进展,设计和合成选择性的激酶抑制剂。
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成果阅读
442
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成果数
6
秦勇, Jun Yang, Hao Song, Xue Xiao, Jue Wang, and Yong Qin*
,-0001,():
-1年11月30日
Starting from tryptamine 4 and isatin 5, a biomimetic approach to the pentacyclic substructure 1 of perophoramidine and communesin was developed. The key steps were to create a stable three/six bicyclic system 2 on the 2,3-double bond of an indole derivative 3 by an intramolecular cyclopropanation, followed by ring opening of the resulting cyclopropane ring with the in situ generated amine group of an aniline.
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【期刊论文】Selective Diethylzinc Reduction of Imines in the Presence of Ketones Catalyzed by Ni(acac)2
秦勇, Xue Xiao, Haowei Wang, Zhiyan Huang, Jun Yang, Xiaoxia Bian, and Yong Qin*
Org. Lett., Vol. 8, No.1, 2006,-0001,():
-1年11月30日
A selective reduction method of an electronically deficient imine in the presence of ketone was developed by employing Et2Zn and 5 mol % of Ni(acac)2. The method was applied in the reduction of SS-tert-butanesulfinyl ketimines 1 to afford amines 2 in 23-92% yields and 73:27 to 98:2 diastereoselectivities. A plausible mechanism was proposed on the basis of an NMR study.
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【期刊论文】Synthesis of Enantiopure tert-Butanesulfinamide from tert-Butanesulfinyloxazolidinone
秦勇, Yong Qin, *, †, Canhui Wang, ‡, Zhiyan Huang, Xue Xiao, † and Yaozhong Jiang*
J. Org. Chem, Vol. 69, No.24, 2004,-0001,():
-1年11月30日
A three-step procedure for the preparation of enantiopure tert-butanesulfinamide 6 in 51% overall yield is described starting from (1R,2S)-N-Cbz-1,2-diphenylaminoethanol. The key step is the reaction of tert-butylmagnesium chloride with N-Cbz-4,5-diphenyl-1,2,3-oxathiazolidine-2-oxide 2 to afford the optical pure tert-butylsulfinyl-4,5-diphenyl-1,3-oxazolidinone 5 via an 1,5-alkoxy anion rearrangement, which is then subject to ammonia hydrolysis with LiNH2 in liquid ammonia to give (R)-tert-butanesulfinamide 6.
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秦勇, Yin Wang, Qin-Fei He, Hao-Wei Wang, Xuan Zhou, Zhi-Yan Huang, and Yong Qin*
J. Org. Chem. 2006, 71, 1588-1591,-0001,():
-1年11月30日
The taxol side chain (SR,2R,3S)-N-tert-butanesulfinyl-O-Boc-3-phenylisoserine benzyl ester 4c was synthesized through a lithium enolate addition of O-Boc-R-hydroxyacetate benzyl ester 5c to benzylidene (SR)-tert-butanesulfinamide 6a in excellent yield and diastereoselectivity. By similar approach, a series of enantiopure 3-substituted isoserine benzyl esters 4 useful for the semi-syntheses of taxol derivatives were also prepared in high to excellent yields and diastereoselectivities. The diastereoselective addition mechanism was discussed on the basis of the experimental observation.
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秦勇, Martin E. Kuehne, *, Yong Qin, and Anne E. Huot†
J. Org. Chem. 2001, 66, 5317-5328,-0001,():
-1年11月30日
The synthesis of 16a
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【期刊论文】Interaction of Tubulin with a New Fluorescent Analogue of Vinblastine†,‡
秦勇, Sabarni K. Chatterjee, §, Julien Laffray, Pruthvi Patel, Rudravajhala Ravindra, Yong Qin, ⅡMartin E. Kuehne, Ⅱ and Susan L. Bane*
Biochemistry 2002, 41, 14010-14018,-0001,():
-1年11月30日
Vinblastine is an antimitotic agent that has been used extensively in cancer chemotherapy. The biological effects of the drug are believed to be the result of its interaction with tubulin, the major component of cellular microtubules. Fluorescence spectroscopy is a powerful and versatile technique for studying drug-tubulin interactions, but it rarely has been applied to studies involving vinca alkaloids. We have prepared a new fluorescent derivative of vinblastine designed to retain high affinity for tubulin while possessing a fluorophore that absorbs and emits visible light. A coumarin derivative of vinblastine, 17-deacetyl-O-(3-carbonylamino-7-diethylaminocoumarin) vinblastine (F-VLB), was prepared by reaction of 17-deacetylvinblastine with 7-diethylaminocoumarin-3-carbonyl azide. F-VLB was a potent inhibitor of in vitro microtubule assembly (IC50=0.5μM). F-VLB binding to tubulin was inhibited by vinblastine. Tubulin binding induced an increase in the F-VLB emission intensity and shifted the emission maximum to higher energy (from 500 to 480nm). The Stokes shift of tubulin-bound F-VLB was about the same as the Stokes shift of the molecule in ethanol, indicating that the tubulin-bound fluorophore is probably on the exterior of the vinblastine binding site. Unlike vinblastine, F-VLB failed to induce self-assembly of tubulin that could be detected by light scattering or electron microscopy, although some self-association could be detected by analytical ultracentrifugation. Equilibrium binding parameters were quantitatively determined by monitoring the change in fluorescence anisotropy of F-VLB upon tubulin binding. The apparent equilibrium constant for F-VLB binding to tubulin [Ka app=(7.7±0.5×10 4M-1 at 25℃] was identical to the equilibrium constant for vinblastine binding to 2μM tubulin (K1) measured under similar buffer and temperature conditions using ultracentrifugation [Vulevic, B., Lobert, S., and Correia, J. J. (1997) Biochemistry 36, 12828-12835]. Binding allocolchicine to tubulin did not significantly affect F-VLB's affinity for the protein [Ka app=(9.1±0.4×10 4M-1 at 25℃]. Analysis of the steady-state emission spectra yielded a distance between the colchicine and vinca binding sites on tubulin of 40 Å. F-VLB bound to paclitaxel-and glutaraldehyde-stabilized microtubules, with approximately equal affinity. We conclude that F-VLB can be used to obtain information about the vinblastine binding site on tubulin under equilibrium conditions.
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