Jun Chang

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Name: 昌军; Jun Chang

Organization: Fudan University

Department: Department of Natural Products Chemistry, School of Pharmacy

Title: Associate Professor

Chemicals
References

Synthesis and biological evaluation of 2-arylimino-3-pyridin-thiazolineone derivatives as antibacterial agents

Co-reporter:Ming-Guang Cai, Yang Wu, Jun Chang

Bioorganic & Medicinal Chemistry Letters 2016 Volume 26(Issue 10) pp:2517-2520

Publication Date(Web):15 May 2016

DOI:10.1016/j.bmcl.2016.03.089

With an intention to find more potent antibacterial agents, four halogen disubstituted thiazolineone derivatives (2a–d), five halogen monosubstituted thiazolineone derivatives (2e–i), and eleven 2-arylimino-3-pyridin-thiazolineone derivatives (2j–t) were synthesized and screened for their antibacterial activity, bactericidal activity, cytotoxicity, and erythrocyte hemolysis. Most of the synthesized derivatives showed antibacterial activity in inhibiting the growth of S. epidermidis and MRSA, and exhibited safety in the cytotoxicity study on the Vero cells and hemolytic activities test on healthy human erythrocytes. 2-Arylimino-3-pyridin-thiazolineone derivatives not only improved the clog P, but also showed potent antibacterial activity in inhibiting the growth of S. epidermidis and MRSA. In particularly, several compounds (2f, 2i, 2r and 2t) showed bactericidal activity, in which compound 2r displayed the best inhibitory capacity among the synthesized compounds, and further druggability research is on going.2-Arylimino-3-pyridin-thiazolineone derivatives (2j–t) not only improved the clog P, but also showed potent antibacterial activity in inhibiting the growth of S. epidermidis and MRSA. In particularly, several compounds (2f, 2i, 2r and 2t) showed bactericidal activity, in which compound 2r displayed the best inhibitory capacity among the synthesized compounds, and further druggability research is on going.

Three New 24-Nortriterpenoids from the Roots of Ilex asprella

Co-reporter:Kun Jiang;Jun-Qi Bai;Jun-Jie Tan;Shi-Jin Qu;Hong-Feng Luo;Chang-Heng Tan;Da-Yuan Zhu

Helvetica Chimica Acta 2014 Volume 97( Issue 1) pp:64-69

Publication Date(Web):

DOI:10.1002/hlca.201300147

Abstract

Asprellols A–C (1–3, resp.), three new 24-nortriterpenoids, were isolated from the CHCl₃-soluble fraction of 95% EtOH extract of the roots of Ilex asprella, together with a known nortriterpenoid. The structures of the new compounds were elucidated as 2,6β,20β-trihydroxy-3-oxo-11α,12α-epoxy-24-norursa-1,4-dien-28,13β-olide (1), 2,6β-dihydroxy-3-oxo-11α,12α-epoxy-24-norursa-1,4,20(30)-trien-28,13β-olide (2), and 2,6β-dihydroxy-3-oxo-11α,12α-epoxy-24-noroleana-1,4-dien-28,13β-olide (3) on the basis of spectroscopic analyses.

Synthesis and Cytotoxic Evaluation of Novel Platinum(II) Complexes with C2-Asymmetric and C2-Symmetric Chiral Vicinal Diamines

Co-reporter:Chen Zhang;Hongrui Liu;Qing Yang;Xun Sun

Chinese Journal of Chemistry 2013 Volume 31( Issue 1) pp:154-158

Publication Date(Web):

DOI:10.1002/cjoc.201201168

Abstract

A series of new platinum(II) complexes with C₂-asymmetric and C₂-symmetric 1,2-diamines were designed and synthesized by convenient methods, involving samarium diiodide induced reductive coupling as the key step. The results of cytotoxicity showed that compounds (R,R)-11a and (S,S)-11a, two novel platinum(II) complexes with asymmetric 1,2-diamines, exhibited more potent cytotoxicity than that of oxaliplatin against all leukemia cell lines. Interestingly, (R,R)-11a and (S,S)-11a demonstrated less potent activity against three solid cancer cell lines than that of oxaliplatin, which indicated that these two compounds may only selectively inhibit the leukemia cell lines. In contrast, (R,R)-15a and (S,S)-15a, two platinum(II) complexes with symmetric 1,2-diamines, showed similar cytotoxicity to that of oxaliplatin against all leukemia cell lines and more potent activity against solid cancer cell lines. Further flow cytometry data indicated that (R,R)-11a could obviously arrest leukemia K562 cells in G2/M phases.

Neuroprotective effects of mercaptoethylleonurine and mercaptoethylguanidine analogs on hydrogen peroxide-induced apoptosis in human neuronal SH-SY5Y cells

Co-reporter:Zhao-Lin Que, Wen-Jiang Zhou, Jun Chang, Xin-Hua Liu, Jian-Ming Yu, Xun Sun

Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 6) pp:1793-1796

Publication Date(Web):15 March 2013

DOI:10.1016/j.bmcl.2013.01.038

A series of mercaptoethylleonurine and mercaptoethylguanidine derivatives were designed and synthesized. Their neuroprotective effects toward H2O2-induced apoptosis were investigated in human SH-SY5Y cells. The results from these studies identified several potent compounds, with compound 8k emerging as the most effective. Further investigation demonstrated that 8k reduced H2O2-induced activation of mitochondrial apoptosis by inhibiting the expression of Bax and elevating the expression of Bcl-2. Moreover, the molecular mechanism underlying the observed neuroprotective effects of 8k was exerted via the Akt and JNK pathways. Compound 8k can be a lead compound for further discovery of neuroprotective medicine.Novel mercaptoethylleonurine and mercaptoethylguanidine derivatives were designed, synthesized, and evaluated for their neuroprotective effects on H2O2-induced apoptosis in human SH-SY5Y cells, and the mechanism of compound 8k was studied.

Chemical constituents from Chonemorpha griffithii

Co-reporter:Jun-Qi Bai, Kun Jiang, Jun-Jie Tan, Xiao-Hui Qiu, Chang-Heng Tan, Jun Chang, Da-Yuan Zhu

Biochemical Systematics and Ecology 2013 Volume 51() pp:171-174

Publication Date(Web):December 2013

DOI:10.1016/j.bse.2013.08.025

•Phytochemistry of Chonemorpha griffithii was investigated at the first time.•20 compounds were firstly isolated from the genus Chonemorpha.•A new dibenzylbutyrolactone-type lignan was identified by spectroscopic analysis.•Two triterpenoids were considered as the chemotaxonomic markers for the species.Chemical investigation of the aerial part of Chonemorpha griffithii has led to the isolation of 20 compounds, comprising six lignans (1–6), six triterpenoids (7–12), four phenolic acids (13–16), two flavonoids (17 and 18), one cyclitol (19) and one aliphatic acid (20). Among them, 5′-methoxy-7′-oxomatairesinol (1) was identified to be a new lignan. It is the first report of the presence of those compounds in this genus. Two 24-methyl-29-norcycloartane triterpenoids (10 and 11) were considered as the chemotaxonomic markers for the species C. griffithii.

Synthesis and antibacterial activity against Clostridium difficile of novel demethylvancomycin derivatives

Co-reporter:Si-Ji Zhang, Qing Yang, Liang Xu, Jun Chang, Xun Sun

Bioorganic & Medicinal Chemistry Letters 2012 Volume 22(Issue 15) pp:4942-4945

Publication Date(Web):1 August 2012

DOI:10.1016/j.bmcl.2012.06.039

To explore the structure–activity relationships (SAR) of demethylvancomycin (2) and find more effective new chemical entities than known glycopeptides for the treatment of Clostridium difficile (C. difficile), 17 novel N-substituted (N-arylmethylene or -aliphatic substituents) demethylvancomycin derivatives were prepared. These analogues have been evaluated in vitro for their antibacterial activities against C. difficile and Enterococcus faecium (E. faecium). Compounds 5d, 5h, and 5i with N-arylmethylene substituents, structurally similar to Oritavancin, showed more potent antibacterial activity against C. difficile than vancomycin (1) or demethylvancomycin (2). Meanwhile, compound 5k with an undecyl side chain showed the most potent antibacterial activity against E. faecium (vancomycin-resistant strain).Seventeen novel N-substituted demethylvancomycin derivatives were prepared and evaluated in vitro for their antibacterial activities against C. difficile and E. faecium. Compounds 5d, 5h, and 5i showed more potent antibacterial activity against C. difficile, while 5k showed the most potent antibacterial activity against E. faecium.