Chunhao Yang

Name:

Organization: Shanghai Institute of Materia Medica

Department: State Key Laboratory of Drug Research

Title:

Chemicals
References

Pot, atom and step economic synthesis: a diversity-oriented approach to construct 2-substituted pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones

Co-reporter:Haoyue Xiang, Yanhong Chen, Qian He, Yuyuan Xie and Chunhao Yang

RSC Advances 2013 vol. 3(Issue 17) pp:5807-5810

Publication Date(Web):28 Feb 2013

DOI:10.1039/C3RA22909B

A diversity-oriented approach to construct 2-heteroaryl-substituted pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one derivatives via copper-promoted two-step one pot reactions from chromenone derivatives has been developed. Pot, atom and step economy (PASE) were combined in these sequential reactions, and at least six bonds were formed in one pot. A number of drug-like small molecules were prepared quickly and efficiently.

A tandem copper (II)-promoted synthesis of 2-substituted pyrrolo[2,1-f][1,2,4] triazin-4(3H)-ones

Co-reporter:Yanhong Chen, Haoyue Xiang, Cun Tan, Yuyuan Xie, Chunhao Yang

Tetrahedron 2013 69(13) pp: 2714-2719

Publication Date(Web):

DOI:10.1016/j.tet.2013.02.004

One-pot syntheses of novel pyrazole-containing bisphosphonate esters at room temperature

Co-reporter:Haoyue Xiang, Xueyu Qi, Yuyuan Xie, Guangyu Xu and Chunhao Yang

Organic & Biomolecular Chemistry 2012 vol. 10(Issue 38) pp:7730-7738

Publication Date(Web):02 Aug 2012

DOI:10.1039/C2OB25889G

An efficient general synthetic approach has been developed to synthesize pyrazole-containing bisphosphonate (N-BPs) esters from chromenone derivatives via a sequential two-step reaction in one pot at ambient temperature in good to excellent yields. This protocol provides a new convenient method to prepare lipophilic bisphosphonate precursors with potential activities.

A Microwave-Assisted Domino Benzannulation Reaction towards Functionalized Naphthalenes, Quinolines, and Isoquinolines

Co-reporter:Yuqin Wang;Cun Tan;Xiaofei Zhang;Qian He;Yuyuan Xie

European Journal of Organic Chemistry 2012 Volume 2012( Issue 33) pp:6622-6629

Publication Date(Web):

DOI:10.1002/ejoc.201201061

Abstract

An efficient palladium/copper-catalyzed domino reaction was developed to yield functionalized naphthalenes, quinolines, and isoquinolines. The reactions of various substituted 1-phenylprop-2-yn-1-ols containing electron-donating (EDG) and electron-withdrawing (EWG) groups and 1-heteroarylprop-2-yn-1-ols worked well with this procedure. Both electron-rich and -deficient aryl halides were satisfactory substrates for this reaction. This domino benzannulation process involves a Sonogashira cross-coupling reaction, followed by isomerization to a chalcone, and finally an intramolecular condensation reaction.

Discovery and bioactivity of 4-(2-arylpyrido[3′,2′:3,4]pyrrolo[1,2-f][1,2,4]triazin-4-yl) morpholine derivatives as novel PI3K inhibitors

Co-reporter:Jia Wang, Xiang Wang, Yanhong Chen, Simeng Chen, Guang Chen, Linjiang Tong, Linghua Meng, Yuyuan Xie, Jian Ding, Chunhao Yang

Bioorganic & Medicinal Chemistry Letters 2012 Volume 22(Issue 1) pp:339-342

Publication Date(Web):1 January 2012

DOI:10.1016/j.bmcl.2011.11.003

PI3K is a promising therapeutic target for cancer. With PI-103 as the lead compound, we designed and synthesized 4-(2-arylpyrido[3′,2′:3,4]pyrrolo[1,2-f][1,2,4]triazin-4-yl)morpholine derivatives. 9, 10a, 10d, 10e had the IC50 against PI3Kα comparable with PI-103. All of the compounds showed selectivity over 15 tested protein kinases and anti-proliferative activity at micromolar concentration against several cancer cell lines.

Design, synthesis and biological evaluation of substituted 11H-benzo[a]carbazole-5-carboxamides as novel antitumor agents

Co-reporter:Yu-Qin Wang, Xiao-Hua Li, Qian He, Yi Chen, Yu-Yuan Xie, Jian Ding, Ze-Hong Miao, Chun-Hao Yang

European Journal of Medicinal Chemistry 2011 Volume 46(Issue 12) pp:5878-5884

Publication Date(Web):December 2011

DOI:10.1016/j.ejmech.2011.09.050

A series of novel 11H-benzo[a]carbazole-5-carboxamide derivatives were designed, synthesized and evaluated for their antitumor activity against human cancer A549 and HCT-116 cell lines. Most of the compounds showed potent antitumor activities, and compound 8 displayed remarkable in vitro and in vivo anticancer activity comparable to that of amonafide.A series of novel 11H-benzo[a]carbazole-5-carboxamide derivatives were designed, synthesized and evaluated for their antitumor activity against human cancer A549 and HCT-116 cell lines. Compound 8 displayed remarkable in vitro and in vivo anticancer activity comparable to that of amonafide.Highlights► A series of novel 11H-benzo[a]carbazole-5-carboxamide derivatives were synthesized. ► Synthesized compounds were evaluated against human cancer A549 and HCT-116 cell lines. ► The most potent compound 8 can be prepared to the physiologically acceptable salt which improves the solubility greatly. ► Compound 8 displayed remarkable in vitro and in vivo anticancer activity comparable to that of amonafide.

Solvent-free synthesis of δ-carbolines/carbazoles from 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives using DPPE as a reducing agent

Co-reporter:Haixia Peng, Xuxing Chen, Yanhong Chen, Qian He, Yuyuan Xie, Chunhao Yang

Tetrahedron 2011 67(32) pp: 5725-5731

Publication Date(Web):

DOI:10.1016/j.tet.2011.06.027

Novel Rhein Analogues as Potential Anticancer Agents

Co-reporter:Dr. Xiaochuan Yang;Dr. Guojing Sun;Dr. Chunhao Yang; Binghe Wang

ChemMedChem 2011 Volume 6( Issue 12) pp:2294-2301

Publication Date(Web):

DOI:10.1002/cmdc.201100384

Abstract

Two series of rhein analogues were synthesized with modification at the 3-position. Their cytotoxicities were evaluated using an MTT assay. Among all the compounds synthesized, one compound showed the best potency, with an IC₅₀ value of 2.7 μM against the HeLa cell line and 0.6 μM against the MOLT4 cell line.

Direct Palladium-Catalyzed Arylations of Aryl Bromides with 2/9-Substituted Pyrimido[5,4-b]indolizines

Co-reporter:Min Jiang, Ting Li, Linghua Meng, Chunhao Yang, Yuyuan Xie and Jian Ding

ACS Combinatorial Science 2009 Volume 11(Issue 5) pp:806

Publication Date(Web):July 31, 2009

DOI:10.1021/cc800162k

C-5 arylated 2/9-substituted pyrimido[5,4-b]indolizines were synthesized via palladium-catalyzed direct arylation. A variety of substituents on both pyrimido[5,4-b]indolizines and aryl/heteroaryl bromides are tolerated, providing rapid access to substituted pyrimido[5,4-b]indolizines in good to excellent yields.

Facile Synthesis of 1,2,3,4-Tetrahydrobenzo[b][1,8]-naphthyridin-2-one via Baylis-Hillman Adducts

Co-reporter:Dongdong CHEN;Jing XU;Yuyuan XIE

Chinese Journal of Chemistry 2009 Volume 27( Issue 4) pp:787-790

Publication Date(Web):

DOI:10.1002/cjoc.200990131

Abstract

Various benzo[b][1,8]naphthyridin-2-ones were synthesized by a one-pot tandem reduction-double cyclization from the corresponding (Z)-ethyl 4-cyano-5-(2-nitrophenyl)-pent-4-enoates, which were easily prepared via Johnson-Claisen rearrangement from Baylis-Hillman affixtures of 2-nitrobenzaldehydes. The procedure has the advantages of easy handling and seperation under mild and green conditions, and the overall yields are moderate.

Aza analogues of equol: Novel ligands for estrogen receptor β

Co-reporter:Wuhong Chen, Zhaohu Lin, Mengmeng Ning, Chunhao Yang, Xueming Yan, Yuyuan Xie, Xu Shen, Ming-Wei Wang

Bioorganic & Medicinal Chemistry 2007 Volume 15(Issue 17) pp:5828-5836

Publication Date(Web):1 September 2007

DOI:10.1016/j.bmc.2007.05.071

3-Aryl-tetrahydroquinolines, aza analogues of equol, are synthesized and evaluated for their binding properties to the estrogen receptors ERα and ERβ. Several of these compounds exhibited binding selectivity for ER similar to that of genistein. Compounds 8c and 8d were found to have dual actions: antagonists for ERα and agonists for ERβ in a yeast two-hybrid assay. These compounds have no estrogenic effects on the uterus and bone in vivo.

Benzothieno[3,2-b]indole derivatives as potent selective estrogen receptor modulators

Co-reporter:Qinggang Ji, Jie Gao, Junbo Wang, Chunhao Yang, Xin Hui, Xueming Yan, Xihan Wu, Yuyuan Xie, Ming-Wei Wang

Bioorganic & Medicinal Chemistry Letters 2005 Volume 15(Issue 11) pp:2891-2893

Publication Date(Web):2 June 2005

DOI:10.1016/j.bmcl.2005.03.111

A series of estrogen receptor ligands based on benzothieno[3,2-b]indole were synthesized and their binding affinity for estrogen receptor subtypes (ERα and ERβ) and effects on mouse uterus and bone were evaluated. Some of these compounds showed strong binding affinity to ER and significantly increased the bone mineral density of ovariectomized mice.A series of benzothieno[3,2-b]indole SERMs were prepared, and their binding affinities for estrogen receptor subtypes (ERα and ERβ) and effects on mouse uterus and bone were evaluated.

One-pot syntheses of novel pyrazole-containing bisphosphonate esters at room temperature

Co-reporter:Haoyue Xiang, Xueyu Qi, Yuyuan Xie, Guangyu Xu and Chunhao Yang

Organic & Biomolecular Chemistry 2012 - vol. 10(Issue 38) pp:NaN7738-7738

Publication Date(Web):2012/08/02

DOI:10.1039/C2OB25889G