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Dive into the research topics where Hongbin Zou is active.

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Featured researches published by Hongbin Zou.


Organic Letters | 2011

One-pot multicomponent approach to indolizines and pyrido[1,2-a]indoles.

Huajian Zhu; Joachim Stöckigt; Yongping Yu; Hongbin Zou

A new synthetic protocol for efficient and regiospecifc assembly of indolizines and pyrido[1,2-a]indoles by coupling of substituted methyl bromides and alkynes with corresponding pyrrole-2-carboxaldehyde and 1H-indole-2-carboxaldehyde has been developed. Additionally, a possible mechanism for the reaction is proposed.


Organic Letters | 2010

Domino Approach for the Synthesis of Pyrrolo[1,2-α]pyrazine from Vinyl Azides

Wenteng Chen; Miao Hu; Jianwei Wu; Hongbin Zou; Yongping Yu

A domino synthesis of pyrrolo[1,2-alpha]pyrazine from 1H-2-pyrrolecarbaldehyde and readily synthesized vinyl azides was developed. This reaction proceeded under relatively mild conditions in the presence of base. Additionally, a possible mechanism for the entire sequence is proposed.


Journal of the American Chemical Society | 2012

Scaffold Tailoring by a Newly Detected Pictet–Spenglerase Activity of Strictosidine Synthase: From the Common Tryptoline Skeleton to the Rare Piperazino-indole Framework

Fangrui Wu; Huajian Zhu; Lianli Sun; Chitra Rajendran; Meitian Wang; Xin Ren; Santosh Panjikar; Artem Cherkasov; Hongbin Zou; Joachim Stöckigt

The Pictet-Spenglerase strictosidine synthase (STR1) has been recognized as a key enzyme in the biosynthesis of some 2000 indole alkaloids in plants, some with high therapeutic value. In this study, a novel function of STR1 has been detected which allows for the first time a simple enzymatic synthesis of the strictosidine analogue 3 harboring the piperazino[1,2-a]indole (PI) scaffold and to switch from the common tryptoline (hydrogenated carboline) to the rare PI skeleton. Insight into the reaction is provided by X-ray crystal analysis and modeling of STR1 ligand complexes. STR1 presently provides exclusively access to 3 and can act as a source to generate by chemoenzymatic approaches libraries of this novel class of alkaloids which may have new biological activities. Synthetic or natural monoterpenoid alkaloids with the PI core have not been reported before.


Organic Letters | 2010

Synthesis of Polysubstituted 5-Aminooxazoles from α- Diazocarbonyl Esters and α-Isocyanoacetamides

Jianwei Wu; Wenteng Chen; Miao Hu; Hongbin Zou; Yongping Yu

A novel and efficient reaction for the synthesis of 2-keto-5-aminooxazoles is developed. The entire sequence is realized by simply heating a xylene solution of alpha-diazocarbonyl esters and alpha-isocyanoacetamides without any promoters. A possible mechanism for the entire sequence is proposed.


Chemistry-an Asian Journal | 2010

A facile chemoenzymatic approach: one-step syntheses of monoterpenoid indole alkaloids.

Hongbin Zou; Huajian Zhu; Liang Zhang; Liuqing Yang; Yongping Yu; Joachim Stöckigt

Facile chemoenzymatic syntheses of cytotoxic monoterpenoid indole alkaloids with novel skeletons and multiple chiral centers are described. Synthesis of these alkaloids was achieved by a simple one-step reaction using strictosidine and 12-aza-strictosidine as the key intermediates. Strictosidines were prepared by coupling of secologanin with tryptamine and 7-aza-tryptamine, respectively, using the immobilized recombinant Rauvolfia strictosidine synthase. A detailed stereochemical analysis is presented herein. The results provide an opportunity for a chemoenzymatic approach that leads to an increased diversification of complex alkaloids with improved structures and activities.


Bioorganic & Medicinal Chemistry | 2010

Synthesis, biological evaluation, and structure-activity relationship study of novel cytotoxic aza-caffeic acid derivatives.

Hongbin Zou; Hao Wu; Xiangnan Zhang; Yu Zhao; Joachim Stöckigt; Yijia Lou; Yongping Yu

Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl)piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl)prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC(50) values of 0.2, 2.0, 1.7, and 1.1 microM, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner.


European Journal of Medicinal Chemistry | 2011

Synthesis and biological evaluation of 2-indolinone derivatives as potential antitumor agents

Hongbin Zou; Liang Zhang; Jingfeng Ouyang; Marc A. Giulianotti; Yongping Yu

Three series of 3-substituted-indolin-2-ones and azaindolin-2-ones have been synthesized and showed potential antiproliferative activity to cancer cell lines. The inhibition activities on VEGF-induced VEGFR phosphorylation were observed for selected 2-indolinones. Among the compounds synthesized, 5-fluoroindolin-2-one derivative 23 with a pyridone unit showed the most significant enzymatic and cellular activities. Flow cytometric analysis indicates that 23 plays a role in suppressing HCT-116 cell proliferation via G1 phase arrest and apoptosis in a dose dependent manner. The binding mode of compound 23 complexed with VEGFR-2 was predicted using FlexX algorithm. Described here are the chemistry and biological testing for these series which will guide the design and optimization of novel 2-indolione antitumor agents.


Chemistry & Biodiversity | 2010

Improved Expression of His6‐Tagged Strictosidine Synthase cDNA for Chemo‐Enzymatic Alkaloid Diversification

Liuqing Yang; Hongbin Zou; Huajian Zhu; Martin Ruppert; Jingxu Gong; Joachim Stöckigt

Strictosidine synthase (STR1) catalyzes the stereoselective formation of 3α(S)‐strictosidine from tryptamine and secologanin. Strictosidine is the key intermediate in the biosynthesis of 2,000 plant monoterpenoid indole alkaloids, and it is a key precursor of enzyme‐mediated synthesis of alkaloids. An improved expression system is described which leads to optimized His6‐STR1 synthesis in Escherichia coli. Optimal production of STR1 was achieved by determining the impact of co‐expression of chaperones pG‐Tf2 and pG‐LJE8. The amount and activity of STR1 was doubled in the presence of chaperone pG‐Tf2 alone. His6‐STR1 immobilized on Ni‐NTA can be used for enzymatic synthesis of strictosidines on a preparative scale. With the newly co‐expressed His6‐STR1, novel 3α(S)‐12‐azastrictosidine was obtained by enzymatic catalysis of 7‐azatryptamine and secologanin. The results obtained are of significant importance for application to chemo‐enzymatic approaches leading to diversification of alkaloids with novel improved structures.


Chemico-Biological Interactions | 2014

Generation of insulin-producing cells from rat mesenchymal stem cells using an aminopyrrole derivative XW4.4.

Jingfeng Ouyang; Wei Huang; Wanwan Yu; Wei Xiong; Ramanjaneya V.R. Mula; Hongbin Zou; Yongping Yu

Type 1 diabetes mellitus (T1DM), a multisystem disease with both biochemical and anatomical/structural consequences, is a major health concern worldwide. Pancreatic islet transplantation provides a promising treatment for T1DM. However, the limited availability of islet tissue or new sources of insulin producing cells (IPCs) that are responsive to glucose hinder this promising approach. Though slow, the development of pancreatic beta-cell lines from rodent or human origin has been steadily progressing. Bone marrow-derived mesenchymal stem cells (MSCs) are multipotent, culture-expanded, non-hematopoietic cells that are currently being investigated as a novel cellular therapy. The in vitro differentiation potential of IPCs has raised hopes for a treatment of clinical diseases associated with autoimmunity. We screened for small molecules that induce pancreatic differentiation of IPCs. There are some compounds which showed positive effects on the DTZ staining. The aminopyrrole derivative compound XW4.4 which shows the best activity among them was found to induce pancreatic differentiation of rat MSCs (rMSCs). The in vitro studies indicated that treatment of rMSCs with compound XW4.4 resulted in differentiated cells with characteristics of IPCs including islet-like clusters, spherical, grape-like morphology, insulin secretion, positive for dithizone, glucose stimulation and expression of pancreatic endocrine cell marker genes. The data has also suggested that hepatocyte nuclear factor 3β (HNF 3β) may be involved in pancreatic differentiation of rMSCs when treated with XW4.4. Results indicate that XW4.4 induced rMSCs support the efforts to derive functional IPCs and serve as a means to alleviate limitations surrounding islet cell transplantation in the treatment of T1DM.


Synthetic Communications | 2009

2,2′-Biimidazole as an Efficient Ligand for Copper(I)-Catalyzed C‒N Coupling Reactions

Zhang Hu; Wei Ye; Hongbin Zou; Yongping Yu

An efficient copper(I)-catalyzed system using 2,2′-biimidazole as the ligand was applied to N-arylation of a broad spectrum of nitrogen nucleophiles with aryl halides. The reactions were carried out in relatively mild conditions with good to excellent yields.

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Hao Wu

Zhejiang University

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Jia Qu

Wenzhou Medical College

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