Literature DB >> 24900297

Synthesis and SAR of Thiazolylmethylphenyl Glucoside as Novel C-Aryl Glucoside SGLT2 Inhibitors.

Kwang-Seop Song1, Suk Ho Lee1, Min Ju Kim1, Hee Jeong Seo1, Junwon Lee1, Sung-Han Lee1, Myung Eun Jung1, Eun-Jung Son1, MinWoo Lee1, Jeongmin Kim1, Jinhwa Lee1.   

Abstract

Novel C-aryl glucoside SGLT2 inhibitors containing the thiazole motif were designed and synthesized for biological evaluation. Among the compounds assayed, thiazole containing furanyl moiety 14v and thiophenyl moiety 14y demonstrated the best in vitro inhibitory activity against SGLT2 in this series to date (IC50 = 0.720 nM for 14v and IC50 = 0.772 nM for 14y). Both of these compounds have been further evaluated on a urinary glucose excretion test and the urine volumes excreted.

Entities:  

Keywords:  SAR; SGLT2; Thiazole; diabetes; glucoside

Year:  2010        PMID： 24900297      PMCID： PMC4018110          DOI： 10.1021/ml100256c

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  13 in total

Review 1.  Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.

Authors:  William N Washburn
Journal:  J Med Chem       Date:  2009-04-09       Impact factor: 7.446

2.  Sergliflozin, a novel selective inhibitor of low-affinity sodium glucose cotransporter (SGLT2), validates the critical role of SGLT2 in renal glucose reabsorption and modulates plasma glucose level.

Authors:  Kenji Katsuno; Yoshikazu Fujimori; Yukiko Takemura; Masahiro Hiratochi; Fumiaki Itoh; Yoshimitsu Komatsu; Hideki Fujikura; Masayuki Isaji
Journal:  J Pharmacol Exp Ther       Date:  2006-10-18       Impact factor: 4.030

3.  Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: Pyridazinylmethylphenyl glucoside congeners.

Authors:  Min Ju Kim; Junwon Lee; Suk Youn Kang; Sung-Han Lee; Eun-Jung Son; Myung Eun Jung; Suk Ho Lee; Kwang-Seop Song; MinWoo Lee; Ho-Kyun Han; Jeongmin Kim; Jinhwa Lee
Journal:  Bioorg Med Chem Lett       Date:  2010-04-09       Impact factor: 2.823

Review 4.  Diabetes update.

Authors:  Arcot Dwarakanathan
Journal:  J Insur Med       Date:  2006

5.  Discovery of canagliflozin, a novel C-glucoside with thiophene ring, as sodium-dependent glucose cotransporter 2 inhibitor for the treatment of type 2 diabetes mellitus.

Authors:  Sumihiro Nomura; Shigeki Sakamaki; Mitsuya Hongu; Eiji Kawanishi; Yuichi Koga; Toshiaki Sakamoto; Yasuo Yamamoto; Kiichiro Ueta; Hirotaka Kimata; Keiko Nakayama; Minoru Tsuda-Tsukimoto
Journal:  J Med Chem       Date:  2010-09-09       Impact factor: 7.446

6.  Pyrimidinylmethylphenyl glucoside as novel C-aryl glucoside SGLT2 inhibitors.

Authors:  Junwon Lee; Jong Yup Kim; Jungsub Choi; Sung-Han Lee; Jeongmin Kim; Jinhwa Lee
Journal:  Bioorg Med Chem Lett       Date:  2010-09-29       Impact factor: 2.823

7.  Biophysical characteristics of the pig kidney Na+/glucose cotransporter SGLT2 reveal a common mechanism for SGLT1 and SGLT2.

Authors:  B Mackenzie; D D Loo; M Panayotova-Heiermann; E M Wright
Journal:  J Biol Chem       Date:  1996-12-20       Impact factor: 5.157

8.  Dapagliflozin, a selective SGLT2 inhibitor, improves glucose homeostasis in normal and diabetic rats.

Authors:  Songping Han; Deborah L Hagan; Joseph R Taylor; Li Xin; Wei Meng; Scott A Biller; John R Wetterau; William N Washburn; Jean M Whaley
Journal:  Diabetes       Date:  2008-03-20       Impact factor: 9.461

9.  Aglycone exploration of C-arylglucoside inhibitors of renal sodium-dependent glucose transporter SGLT2.

Authors:  Bruce A Ellsworth; Wei Meng; Manorama Patel; Ravindar N Girotra; Gang Wu; Philip M Sher; Deborah L Hagan; Mary T Obermeier; William G Humphreys; James G Robertson; Aiying Wang; Songping Han; Thomas L Waldron; Nathan N Morgan; Jean M Whaley; William N Washburn
Journal:  Bioorg Med Chem Lett       Date:  2008-07-31       Impact factor: 2.823

10.  Discovery of dapagliflozin: a potent, selective renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.

Authors:  Wei Meng; Bruce A Ellsworth; Alexandra A Nirschl; Peggy J McCann; Manorama Patel; Ravindar N Girotra; Gang Wu; Philip M Sher; Eamonn P Morrison; Scott A Biller; Robert Zahler; Prashant P Deshpande; Annie Pullockaran; Deborah L Hagan; Nathan Morgan; Joseph R Taylor; Mary T Obermeier; William G Humphreys; Ashish Khanna; Lorell Discenza; James G Robertson; Aiying Wang; Songping Han; John R Wetterau; Evan B Janovitz; Oliver P Flint; Jean M Whaley; William N Washburn
Journal:  J Med Chem       Date:  2008-02-09       Impact factor: 7.446
View more
  1 in total

Review 1.  Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents.

Authors:  Mohammed F Arshad; Aftab Alam; Abdullah Ayed Alshammari; Mohammed Bader Alhazza; Ibrahim Mohammed Alzimam; Md Anish Alam; Gulam Mustafa; Md Salahuddin Ansari; Abdulelah M Alotaibi; Abdullah A Alotaibi; Suresh Kumar; Syed Mohammed Basheeruddin Asdaq; Mohd Imran; Pran Kishore Deb; Katharigatta N Venugopala; Shahamah Jomah
Journal:  Molecules       Date:  2022-06-21       Impact factor: 4.927
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.