Synthesis and biological evaluation of sulfonamide analogues of the phosphatidylinositol 3-kinase inhibitor ZSTK474

被引：14

作者：

Gamage, Swarna A. ^{[1
]}

Giddens, Anna C. ^{[1
]}

Tsang, Kit Y. ^{[1
]}

Flanagan, Jack U. ^{[1
,2
]}

Kendall, Jackie D. ^{[1
,2
]}

Lee, Woo-Jeong ^{[3
]}

Baguley, Bruce C. ^{[1
,2
]}

Buchanan, Christina M. ^{[2
,3
]}

Jamieson, Stephen M. F. ^{[1
,2
]}

Shepherd, Peter R. ^{[1
,2
,3
]}

Denny, William A. ^{[1
,2
]}

Rewcastle, Gordon W. ^{[1
,2
]}

机构：

[1] Univ Auckland, Fac Med & Hlth Sci, Auckland Canc Soc, Res Ctr, Private Bag 92019, Auckland 1142, New Zealand

[2] Univ Auckland, Maurice Wilkins Ctr Mol Biodiscovery, Private Bag 92019, Auckland 1142, New Zealand

[3] Univ Auckland, Fac Med & Hlth Sci, Dept Mol Med & Pathol, Private Bag 92019, Auckland 1142, New Zealand

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2017年 / 25卷 / 20期

关键词：

Phosphatidylinositol; 3-kinase; PI3K; p110; alpha; ZSTK474; PHOSPHOINOSITIDE; 3-KINASE; CLASS-I; PI3K INHIBITOR; ISOFORM SELECTIVITY; BREAST-CANCER; PIK3CA GENE; DISCOVERY; PATHWAY; KINASE; MECHANISMS;

D O I：

10.1016/j.bmc.2017.09.025

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Replacement of one of the morpholine groups of the phosphatidylinositol 3-kinase (PI3K) inhibitor ZSTK474 (1) with sulfonamide containing substituents produced a new class of active and potent PI3K alpha inhibitors. Solubility issues prevented all but the 6-amino derivative 17 from being evaluated in vivo, but the clear activity of this compound demonstrated that this class of PI3K inhibitor shows great promise. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：5859 / 5874

页数：16

共 50 条

[31] Immune-mediated antitumor effects of a pan PI3K inhibitor ZSTK474
Isoyama, Sho
Sugiyama, Daisuke
Nishikawa, Hiroyoshi
CANCER SCIENCE, 2018, 109 : 221 - 221
[32] ZSTK474, a Specific PI3K Inhibitor, Induces Mesenchymal to Epithelial Transition in Vivo
Okamura, M.
Dan, S.
Yoshimi, H.
Yamori, T.
EUROPEAN JOURNAL OF CANCER, 2012, 48 : 109 - 109
[33] A SPECIFIC INHIBITOR OF PHOSPHATIDYLINOSITOL 3-KINASE
VLAHOS, CJ
MATTER, WF
BROWN, RF
JOURNAL OF CELLULAR BIOCHEMISTRY, 1994, : 274 - 274
[34] Induction of apoptosis by ZSTK474, a PI3K inhibitor in chromosomal translocation-positive sarcoma
Isoyama, Sho
Tamaki, Naomi
Dan, Shingo
CANCER SCIENCE, 2021, 112 : 894 - 894
[35] Potential antitumor effect of a pan-PI3K inhibitor ZSTK474 on human sarcoma cell lines
Dan, Shingo
Tamaki, Naomi
Namatame, Nachi
Yoshizawa, Yuya
Okamura, Mutsumi
Nishimura, Yumiko
Yamazaki, Kanami
Yaguchi, Shin-ichi
CANCER RESEARCH, 2019, 79 (13)
[36] Synthetic studies of the phosphatidylinositol 3-kinase inhibitor LY294002 and related analogues
Abbott, B
Thompson, P
AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (11) : 1099 - 1106
[37] Synthesis and biological evaluation of novel phosphatidylinositol 3-kinase inhibitors: Solubilized 4-substituted benzimidazole analogs of 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474)
Rewcastle, Gordon W.
Gamage, Swarna A.
Flanagan, Jack U.
Kendall, Jackie D.
Denny, William A.
Baguley, Bruce C.
Buchanan, Christina M.
Chao, Mindy
Kestell, Philip
Kolekar, Sharada
Lee, Woo-Jeong
Lill, Claire L.
Malik, Alisha
Singh, Ripudaman
Jamieson, Stephen M. F.
Shepherd, Peter R.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 64 : 137 - 147
[38] ZSTK474, a PI3K inhibitor, exerts an antitumor effect against synovial sarcoma in vitro and in vivo
Tamaki, Naomi
Namatame, Nachi
Okamura, Mutsumi
Yaguchi, Shin-ichi
Dan, Shingo
CANCER SCIENCE, 2018, 109 : 1006 - 1006
[39] ZSTK474, a PI3K inhibitor, suppresses proliferation and sensitizes human pancreatic adenocarcinoma cells to gemcitabine
Duong, Hong-Quan
Kim, Hee Jeong
Kang, Hyo Jin
Seong, Yeon-Sun
Bae, Insoo
ONCOLOGY REPORTS, 2012, 27 (01) : 182 - 188
[40] Dual effects of the PI3K inhibitor ZSTK474 on multidrug efflux pumps in resistant cancer cells
Muthiah, Divya
Callaghan, Richard
EUROPEAN JOURNAL OF PHARMACOLOGY, 2017, 815 : 127 - 137

← 1 2 3 4 5 →