苗志伟
个性化签名
- 姓名:苗志伟
- 目前身份:
- 担任导师情况:
- 学位:
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学术头衔:
- 职称:-
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学科领域:
有机化学
- 研究兴趣:
苗志伟,1987年9月-1991年7月,天津师范大学化学系获理学学士学位;1994年9月-1998年3月,天津师范大学化学系物理化学专业获理学硕士学位;1999年9月-2002年7月,清华大学化学系有机化学专业获理学博士学位;2002年10月-2004年10月,苏黎世瑞士联邦高等理工大学(ETH Zürich)化学系有机化学专业博士后。
工作经历:
2004年10月-今,南开大学元素有机化学研究所,副教授;1998年3月-1999年10月,天津师范大学化学系,讲师;1991年7月-1998年3月,天津师范大学化学系,辅导员、团总支书记。
主讲课程:
本科生:有机化学、有机化学实验。
研究领域:
有机合成化学、有机磷化学、药物化学
研究课题:
1、 酶抑制剂的设计、合成及构效关系研究
以亮氨酸氨基肽酶为靶位来设计酶抑制剂,根据酶的三维结构和酶与底物的作用特性,设计、合成一系列特定化合物,从中筛选出具有高效抑制活性的抑制剂,并通过NMR、质谱和X-射线晶体衍射分析等方法研究酶与抑制剂的相互作用机理。利用SGI工作站进行构效关系研究,通过分子模拟和分子对接等技术对底物的分子结构进行修饰,为合成结构新颖的底物分子提供结构信息。
2、 具有生物活性有机磷化合物的合成
α-氨基膦酸及其衍生物具有广泛的生物和药物活性,利用类Mannich反应通过路易斯酸催化“一锅法”合成α-氨基膦酸衍生物,特别是通过手性诱导方法实现α-氨基膦酸衍生物的不对称合成。
3、 有机催化剂的研究
设计、合成具有特定结构的有机化合物,用于催化有机化合物的不对称合成。
4、 生物缀合物的合成与活性研究
生物缀合物可以将药物分子与载体结合起来成为前药(Prodrugs),利用载体的不同性质可以增强药物分子的稳定性,提高药物分子的选择性,降低毒副作用。
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成果阅读
512
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成果数
10
苗志伟, B. Wang, , Z. W. Miao, J. Wang, R. Y. Chen, X. D. Zhang
Amino Acids (2007),-0001,():
-1年11月30日
A series of novel naphthoquinone fused cyclic α-aminophosphonates, 2-alkoxy-3, 4-dihydro-2H-naphtho[2,3-e][1,4,2] oxazaphosphinane-5, 10-dione 2-oxide 3–17 and naphthoquinone fused cyclic α-aminophosphonic monoester 18 were synthesized for the first time. These cyclic α-aminophosphonates were evaluated for antitumor activity on four human tumor cell lines, and three of them showed significant cytotoxicity (IC50: 0.019–5.15 μM) comparable to that of the reference drug doxorubicin. Furthermore, inhibition assays for topoisomerase II-mediated relaxation of supercoiled DNA indicated that the naphthoquinone fused cyclic aminophosphonates were catalytic inhibitors of topoisomerase II.
Amino acid, Aminoalkylphosphonic acid, Topoisomerase II inhibitors, Mannich-type reaction, Phosphorus heterocycles
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苗志伟, Jianfeng Zhang, Zhanwei Cui, Fei Wang, Yadan Wang, Zhiwei Miao, Ruyu Chen
Green Chem., 2007, 9, 1341–1345,-0001,():
-1年11月30日
A convenient and rapid method was developed for the synthesis of various N-phosphoramino α-aminoalkylphosphonates through Mannich type reactions under catalyst- and solvent-free conditions with excellent yields.
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【期刊论文】Synthesis of Diphenyl α-(Dipropoxyphosphoramido) alkyl-phosphonates
苗志伟, CUI Zhan-Wei, ZHANG Jian-Feng, MIAO Zhi-Wei, CHEN Ru-Yu
Chinese Journal of Chemistry, 2007, 25, 1551—1554,-0001,():
-1年11月30日
A convenient method has been developed for the synthesis of diphenyl α-(dipropoxyphosphoramido) alkyl- phosphonates under mild conditions, namely the reaction of dipropyl phosphoramidate (1) with a para-(un)substituted benzaldehyde or cyclicketone (2) and triphenyl phosphite (3) by a one-pot procedure with the aid of acetyl chloride.
Mannich type reaction, α-aminoalkanephosphonate, triphenyl phosphate, acetyl chloride
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苗志伟, MIAO Zhi-Wei, FU Cui-Rong, WANG, Bin, CUI Zhan-Wei, ZHANG Jian-Feng, CHEN Ru-Yu
Chinese Journal of Chemistry, 2007, 25, 1344—1348,-0001,():
-1年11月30日
N-(1,3,2-Dioxaphosphorinan-2-ylmethyl) thiophosphoramidates were synthesized and determined by NMR spectra and positive ion electrospray ionization mass spectrometry (ESI-MS) in conjunction with tandem mass spectrometry (MS/MS). The fragmentation pathways were investigated. The results show that these characteristic ions in ESI mass spectra are useful in the structural determination of N-(1, 3, 2-dioxaphosphorinan-2-ylmethyl)- thiophosphoramidates.
ESI-MS, N-(, 1,, 3,, 2-dioxaphosphorinan-2-ylmethyl), thiophosphoramidate, conjugate, tandem mass spectrometry
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苗志伟, Bin Wang, Zhiwei Miao, Ruyu Chen
Heteroatom Chemistry Volume 18, Number 4, 2007,-0001,():
-1年11月30日
The synthesis of a novel quinone fused phosphorus heterocycle, 2-chloro-3, 3-disub- stituents-3, 4-dihydro-2H-naphtho[2, 3-e][1, 4, 2]-oxazaphosphinane-5, 10-dione 2-oxide (3a–g), was described for the first time. These compounds, which have a readily leaving group Cl, can serve as intermediates of many quinone fused phosphorus heterocycles. The structures of 3a–g were characterized by using common spectroscopic methods. According to the X-ray structure of 3a, these compounds may be used as DNΑ-intercalators.
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【期刊论文】A Convenient Synthesis of 2-Alkoxy-2-oxo-1, 4, 2-oxazaphosphinanes
苗志伟, Bin Wang, Zhiwei Miao, You Huang, Ruyu Chen
Heteroatom Chemistry Volume 18, Number 1, 2007,-0001,():
-1年11月30日
A study on the synthesis of the novel cyclic α-aminophosphonates and 2-alkoxy-2- oxo-1, 4, 2-oxazaphosphinanes 4a–r has been carried out. The title compounds were obtained in good yields by one-pot procedure using o-aminophenol, alkyl dichlorophosphinite, and ketones or benzaldehyde. One of their geometric stereoisomers was isolated and characterized. Configurations of 4k and one isomer of 4r have been established by X-ray diffraction analysis. The synthetic methods provide an easy access to the organophosphorus heterocycles with the ring system mentioned above. The abnormal chemical shifts of alkyl-substitute protons in 1H NMR spectra were given reasonable explanation.
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苗志伟, Zhiwei Miao, Jianfeng Zhang, Zhanwei Cui, Bin Wang, Ruyu Chen
Helvetica Chimica Acta – Vol. 90 (2007),-0001,():
-1年11月30日
A study on the synthesis of the novel N-(cyclic phosphonate)-substituted phosphoramidothioates, i.e., O, O-diethyl N-[(trans-4-aryl-5, 5-dimethyl-2-oxido-2λ5-1, 3, 2-dioxaphosphorinan-2-yl) methyl] phosphoramidothioates 4a–1, from O, O-diethyl phosphoramidothioate (1), a benzaldehyde or ketone 2, and a 1, 3, 2-dioxaphosphorinane 2-oxide 3 was carried out (Scheme 1 and Table 1). Some of their stereoisomers were isolated, and their structure was established. The presence of acetyl chloride was essential for this reaction and accelerated the process of intramolecular dehydration of intermediate 5 forming the corresponding Schiff base 7 (Scheme 2).
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苗志伟, MingXu, Zhiwei Miao, Bruno Bernet, Andrea Vasella
HELVETICA CHIMICA ACTA – Vol. 88 (2005),-0001,():
-1年11月30日
Base-promoted (KOH or MeONa in MeOH, or NaH in THF) cycloisomerisation of partially benzylated, 1-substituted (R=Ph-C≡C, pyridin-2-yl, or Br) ald-1-ynitols leads to (Z)-configured five-, six-, and seven-membered exo-glycals. The reactivity of the ald-1-ynitols depends upon their configuration. The ald-1-ynitols were derived from 2,3,5-tri-O-benzyl-D-ribofuranose 1, and the corresponding, partially O-benzylated galactose, glucose, and mannose hemiacetals by ethynylation. The hex-1-ynitol 2 derived from 1 (61%) was transformed via the 1-phenylbutα-1,3-diyne 3 and the 1-(pyridin-2-yl)acetylene 5 into the five-membered exo-glycals 4 and 6 (in 66 and 72% yields, resp., from 2). The analoguous ethynylation of 2,3,4,6-tetra-O-benzyl-D-galactose 8 was accompanied by elimination of one benzyloxy (BnO) group to the hept-3-en-1-ynitol 9 (71%), which was trans- formed into the non-5-ene-1,3-diynitol 10 and further into the six-membered exo-glycal 11 (50% from 9). Addition of Me3SiC≡CH to the galactose 8 and to the gluco- and manno-analogues 16 and 24 gave epimeric mixtures of the silylated oct-1-ynitols (86% of 12L/12D 45 : 55, 94% of 17L/17D 7 :3, and 86% of 25L/25D 55 :45), which were separated by flash chromatography, and individually transformed into the corresponding 1-bromooct-1-ynitols. Upon treatment with NaH in THF, only the minor epimers 13L, 18D, and 26D cyclised readily to form the seven-membered hydroxy exo-glycals. They were acetylated to the more stable monoacetates 14L, 23D, and 28D (82–89% overall yield). Under the same conditions, the epimers 13D, 18L, and 26L decomposed within 12 h mostly to polar products. The difference of reactivity was rationalised by analysing the consequences of an intramolecular C(3)O-H···—OC(7) H-bond of the intermediate alkoxides on the orientation of —O-C(7) of 13L, 18D, and 26D and its proximity to the ethynyl group.
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苗志伟, Zhiwei Miao, Ming Xu, Barbara Hoffmann, Bruno Bernet, Andrea Vasella
HELVETICA CHIMICA ACTA - Vol. 88 (2005),-0001,():
-1年11月30日
Functionalised bicyclic exo-glycals are readily obtained by base-catalysed (typically MeONa in MeOH) alkynol cycloisomerisation of ethynylated cyclic saccharides. Thus, base treatment of the phenylethynyl- and halogenoethynylated 1-O-acetyl-ribofuranoses 22 - 24 and the 4-ethynylated 1-thioglucopyranosides 30 - 33 gave - after deacetylation - selectively the (Z)-configured exocyclic enol ethers 26 - 28 (84 - 91%) and 34 - 37 (63-76%), respectively, resulting from a trans-5-exo-dig cyclisation. The ring closure to the trans-dioxahex-ahydroindans 34 - 37 is favoured by a concerted intramolecular protonation of the intermediate vinyl anion by the neighbouring HO-C(3). Cycloisomerisation of the 6-O-acetyl-4-(phenylethynyl)-1-thio-α-D-glucopyrano-side 39 occurred via the corresponding phenylethynylated allenes to provide the galacto-configured (Z)- and (E)-cis-dioxahexahydroindans 40 (30%) and 41 (51%). Surprisingly, the HO-C(4) unprotected α-D-galactopyranosyl-butα-1,3-diyne 15 and the β-D-glucopyranosyl-butα-1,3-diyne 51 (and its 2-bromoethynyl analogue) undergo a 6-exo-dig ring closure to the 2,5-dioxabicyclo[2.2.2] octanes 16 - 19 and 52/53, respectively, the ring closure requiring a boat conformation (B1,4 for 15, 1,4B for 51). Ring strain (anti-reflex effect) prevents an alkynol cycloisomerisation of 4-(phenylbuta-1,3-diynyl, bromoethynyl, or iodoethynyl) levoglucosan 56 - 59, and 56 reacted by elimination to the hex-1-ene-3,5-diyne 59 (82%), while isomerisation of 57 and 58 led to epimeric mixtures of the haloallenes 60 (82%) and 61 (68%).
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苗志伟, Zhiwei Miao, Bin Wang, Gaihong Zhang, Ruyu Chen
Bioorganic Chemistry 34 (2006) 167–172,-0001,():
-1年11月30日
An improved method for the synthesis of Diphenyl α-(diethoxythiophosphorylamino) methylphosphonates under mild conditions is described. It consists of the reaction of diethyl thiophosphoramidate (1) with triphenyl phosphite (3) and a substituted benzylaldehyde or ketone (2) by a one-pot procedure with the aid of acetyl chloride.
Mannich type reaction, Thiophosphate-phosphonate derivatives, Acetyl chloride, X-ray crystal structure
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