Structure-based design, synthesis, and SAR evaluation of a new series of 8-hydroxyquinolines as HIF-1α prolyl hydroxylase inhibitors

被引：52

作者：

Warshakoon, Namal C. ^{[1
]}

Wu, Shengde ^{[1
]}

Boyer, Angelique ^{[1
]}

Kawamoto, Richard ^{[1
]}

Sheville, Justin ^{[1
]}

Renock, Sean ^{[1
]}

Xu, Kevin ^{[1
]}

Pokross, Matthew ^{[1
]}

Zhou, Songtao ^{[1
]}

Winter, Carol ^{[1
]}

Walter, Richard ^{[1
]}

Mekel, Marlene ^{[1
]}

Evdokimov, Artem G. ^{[1
]}

机构：

[1] Procter & Gamble Pharmaceut Inc, Drug Discovery Div, Mason, OH 45040 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2006年 / 16卷 / 21期

关键词：

prolyl hydroxylase inhibitors; HIF-1; alpha; hypoxia; ischemia; peripheral arterial disease (PAD); anemia; 8-hydroxyquinolinecarboxyamides;

D O I：

10.1016/j.bmcl.2006.08.040

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new series of potent 8-hydroxyquinolines was designed based on the newly resolved X-ray crystal structure of EGLN-1. Both alkyl and aryl 8-hydroxyquinoline-7-carboxyamides were good HIF-1 alpha prolyl hydroxylase (EGLN) inhibitors. In subsequent VEGF induction assays, these exhibited potent VEGF activity. In addition, this class of compounds did show the ability to stabilize HIF-1 alpha. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5517 / 5522

页数：6

共 50 条

[1] Design and synthesis of substituted pyridine derivatives as HIF-1α prolyl hydroxylase inhibitors
Warshakoon, Namal C.
Wu, Shengde
Boyer, Angelique
Kawamoto, Richard
Sheville, Justin
Bhatt, Ritu Tiku
Renock, Sean
Xu, Kevin
Pokross, Matthew
Zhou, Songtao
Walter, Richard
Mekel, Marlene
Evdokimov, Artem G.
East, Stephen
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (21) : 5616 - 5620
[2] Design and synthesis of a series of novel pyrazolopyridines as HIF 1-α prolyl hydroxylase inhibitors
Warshakoon, Namal C.
Wu, Shengde
Boyer, Angelique
Kawamoto, Richard
Renock, Sean
Xu, Kevin
Pokross, Matthew
Evdokimov, Artem G.
Zhou, Songtao
Winter, Carol
Walter, Richard
Mekel, Marlene
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (21) : 5687 - 5690
[3] A novel series of imidazo[1,2-a]pyridine derivatives as HIF-1α prolyl hydroxylase inhibitors
Warshakoon, Namal C.
Wu, Shengde
Boyer, Angelique
Kawamoto, Richard
Sheville, Justin
Renock, Sean
Xu, Kevin
Pokross, Matthew
Evdokimov, Artem G.
Walter, Richard
Mekel, Marlene
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (21) : 5598 - 5601
[4] Discovery of novel hydroxy-thiazoles as HIF-α prolyl hydroxylase inhibitors:: SAR, synthesis, and modeling evaluation
Tegley, Christopher M.
Viswanadhan, Vellarkad N.
Biswas, Kaustav
Frohn, Michael J.
Peterkin, Tanya A. N.
Chang, Catherine
Burli, Roland W.
Dao, Jennifer H.
Veith, Henrike
Rogers, Norma
Yoder, Sean C.
Biddlecome, Gloria
Tagari, Philip
Allen, Jennifer R.
Hungate, Randall W.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (14) : 3925 - 3928
[5] Structure-based design, synthesis and SAR of a novel series of thiopheneamidine urokinase plasminogen activator inhibitors
Subasinghe, NL
Illig, C
Hoffman, J
Rudolph, MJ
Wilson, KJ
Soll, R
Randle, T
Green, D
Lewandowski, F
Zhang, M
Bone, R
Spurlino, J
DesJarlais, R
Deckman, I
Molloy, CJ
Manthey, C
Zhou, Z
Sharp, C
Maguire, D
Crysler, C
Grasberger, B
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (11) : 1379 - 1382
[6] Dihydropyrazole derivatives as telomerase inhibitors: Structure-based design, synthesis, SAR and anticancer evaluation in vitro and in vivo
Wang, Yang
Cheng, Fei Xiong
Yuan, Xiao Long
Tang, Wen Jian
Shi, Jing Bo
Liao, Chen Zhong
Liu, Xin Hua
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 112 : 231 - 251
[7] Structure-based design, synthesis and biological evaluation of β-glucuronidase inhibitors
Khalid M. Khan
Nida Ambreen
Muhammad Taha
Sobia A. Halim
Shagufta Zaheer-ul-Haq
Saima Naureen
Shahnaz Rasheed
Sajjad Perveen
Mohammad Iqbal Ali
[J]. Journal of Computer-Aided Molecular Design, 2014, 28 : 577 - 585
[8] Structure-based design, synthesis and biological evaluation of β-glucuronidase inhibitors
Khan, Khalid M.
Ambreen, Nida
Taha, Muhammad
Halim, Sobia A.
ul-Haq, Zaheer
Naureen, Shagufta
Rasheed, Saima
Perveen, Shahnaz
Ali, Sajjad
Choudhary, Mohammad Iqbal
[J]. JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 2014, 28 (05) : 577 - 585
[9] Design, synthesis and biological evaluation of potential inhibitors of the HIF-1 \#945;:HIF-1\#946; protein-protein interaction
Bendiabdellah, Yassine
Zinzalla, Giovanna
Badarch, Uranchimeg
Nahar, Kazi
Antonow, Dyeison
Rahman, Khondaker
Shoemaker, Robert
Melillo, Giovanni
Thurston, David
[J]. CANCER RESEARCH, 2009, 69
[10] Structure-Based Design, Synthesis, and Biological Evaluation of Triazole-Based smHDAC8 Inhibitors
Kalinin, Dmitrii, V
Jana, Sunit K.
Pfafenrot, Maxim
Chakrabarti, Alokta
Melesina, Jelena
Shaik, Tajith B.
Lancelot, Julien
Pierce, Raymond J.
Sippl, Wolfgang
Romier, Christophe
Jung, Manfred
Holl, Ralph
[J]. CHEMMEDCHEM, 2020, 15 (07) : 571 - 584

← 1 2 3 4 5 →