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曲格列酮 | 97322-87-7

曲格列酮
Troglitazone
97322-87-7
C24H27NO5S
441.539885759354
如需查看该化合物的详细结构式,mol文件,smile,InChi 请点击:曲格列酮结构式
曲格列酮价格
简介
Troglitazone 是 PPARγ 的激动剂,对人和鼠 PPARγ的 EC50 值分别为 550 nM 和 780 nM。
名称和标识符
MDL MFCD00878416
InChIKey GXPHKUHSUJUWKP-UHFFFAOYSA-N
Inchi 1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)
SMILES O=C1NC(=O)C(CC2C=CC(OCC3(CCC4C(=C(C)C(C)=C(C=4C)O)O3)C)=CC=2)S1
BRN 4338399
别名信息
- 中文别名 -
  • 曲格列酮
  • (+/-)-5-[4-[(6-羟基-2,5,7,8-四甲基苯并二氢吡喃-2-基)甲氧基]苄基]-2,4-噻唑烷二酮
  • 曲格列酮-D4
  • 5-[[4-[(3,4-二氢-6-羟基-2,5,7,8-四甲基-2H-1-苯并吡喃-2-基)甲氧基]苯基]甲基]-2,4-噻唑烷二酮
  • 特洛格列酮
- 英文别名 -
  • Troglitazone
  • (+/-)-5-[4-[(6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl]-2,4-thiazolidinedione
  • 5-[[4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
  • CS-045
  • [14C]-Troglitazone
  • [3H]-Troglitazone
  • 5-[[4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methy
  • 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2,4-dioxothiazolidine
  • 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl-methoxy)-benzyl]thiazolidine-2,4-dione
  • 5-[4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]-benzyl]-2,4-thiazolidinedione
  • Noscal
  • Prelay
  • Rezulin
  • Rezulin (TN)
  • Romglizone
  • Romozin
  • ​EPM-426
  • CS 045
  • GR 92132X
  • GR92132X
  • CI 991
  • C24H27NO5S
  • (+-)-all-rac-5-(p-((6-Hydroxy-2,5,7,8-tetramethyl-2-chromanyl)methoxy)benzyl)-2,4-thiazolidinedione
  • 5-(4-(6-Hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl)thiazolidine-2,4-dione
  • CS045
  • GXPHKUHSUJUWKP-UHFFFAOYSA-N
  • DSSTox_CID_3719
  • DSSTox_RID_77162
  • DSSTox_GSID_23719
  • 2,4-Thiazoli
  • 5-[[4-[(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy]phenyl]methyl]-2,4-thiazolidinedione (ACI)
  • Depotox
物化性质
实验特性
LogP 4.70300
PSA 110.16000
沸点 657°C at 760 mmHg
熔点 184-186°C
溶解度 DMSO: 20 mg/mL
颜色与性状 黄色固体
溶解性 不溶于水
计算特性
精确分子量 441.16100
氢键供体数量 2
氢键受体数量 6
可旋转化学键数量 5
重原子数量 31
复杂度 681
同位素原子数量 0
确定原子立构中心数量 0
不确定原子立构中心数量 2
确定化学键立构中心数量 0
不确定化学键立构中心数量 0
共价键单元数量 1
疏水参数计算参考值(XlogP) 5.1
互变异构体数量 45
表面电荷 0
拓扑分子极性表面积 110
国际标准相关数据
EINECS 8969
合成路线

合成路线:1 步

参考文献:
Novel polymorphic Form-5 of troglitazone and a pharmaceutical composition having enhanced antidiabetic activity
, India, , ,

合成路线:1 步

参考文献:
Novel polymorphic Form-6 of troglitazone and a pharmaceutical composition having enhanced antidiabetic activity
, India, , ,

合成路线:1 步

反应条件:
参考文献:
Reduction of the exocyclic double bond of substituted thiazolidine diones by Hantzsch 1,4-dihydropyridine
Hariharakrishnan, Venkatasubramanian; Rao, Bandi Venugopala; Prasad, Kodali Hari, Indian Journal of Heterocyclic Chemistry, 2006, 15(4), 407-408

合成路线:1 步

反应条件:
参考文献:
A short synthesis of troglitazone: an antidiabetic drug for treating insulin resistance
Cossy, Janine; Menciu, Cecilia; Rakotoarisoa, Haja; Kahn, Philippe H.; Desmurs, Jean-Roger, Bioorganic & Medicinal Chemistry Letters, 1999, 9(24), 3439-3440

合成路线:1 步

参考文献:
The research group of Professor Ning Jiao and Song Song made new progress in the field of electrophilic halogenation modification of drugs
Song, Song; Wang, Weijin, Journal of Chinese Pharmaceutical Sciences, 2021, 30(6), 543-544

合成路线:1 步

反应条件:
参考文献:
Preparation of troglitazone
, World Intellectual Property Organization, , ,

合成路线:1 步

参考文献:
Processes for making thiazolidinedione derivatives and compounds thereof
, World Intellectual Property Organization, , ,

合成路线:1 步

参考文献:
Synthesis of troglitazone's synthetic intermediate 2,5-dihydroxy-3,4,6-trimethylacetophenone and its reactive mechanism
Wang, Shaojie; Feng, Yubo; Liu, Renyong; Liang, Yong, Zhongguo Yaowu Huaxue Zazhi, 2000, 10(3), 203-204

合成路线:1 步

反应条件:
参考文献:
Process for the preparation of 2-(aryloxymethyl)-2,5,7,8-tetramethylchroman-6-ols
, World Intellectual Property Organization, , ,

合成路线:1 步

参考文献:
Thiazolidine derivatives for lowering blood lipids and sugar
, Japan, , ,

合成路线:1 步

参考文献:
Novel polymorphic form-4 of troglitazone and a pharmaceutical composition having enhanced anti-diabetic activity
, India, , ,

合成路线:1 步

参考文献:
Process for preparing thiazolidinediones such as pioglitazone via reduction of exocyclic double bonds at the 5-position of thiazolidinediones using dithionite.
, World Intellectual Property Organization, , ,

合成路线:1 步

反应条件:
参考文献:
Synthesis of new troglitazone derivatives: Anti-proliferative activity in breast cancer cell lines and preliminary toxicological study
Salamone, Stephane; Colin, Christelle; Grillier-Vuissoz, Isabelle; Kuntz, Sandra; Mazerbourg, Sabine; et al, European Journal of Medicinal Chemistry, 2012, 51, 206-215

合成路线:1 步

反应条件:
参考文献:
Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium
Fan, Yun-Hua; Chen, Han; Natarajan, Amarnath; Guo, Yuhong; Harbinski, Fred; et al, Bioorganic & Medicinal Chemistry Letters, 2004, 14(10), 2547-2550

合成路线:1 步

反应条件:
参考文献:
Preparation of polymorphic form I of troglitazone having enhanced antidiabetic activity
, India, , ,

合成路线:1 步

参考文献:
Synthetic thiazolidinediones, potential antidiabetic compounds
Ortiz, Aurelio; Sansinenea, Estibaliz, Current Organic Chemistry, 2011, 15(1), 108-127

合成路线:1 步

参考文献:
Novel polymorphic Form-3 of troglitazone and a pharmaceutical composition having enhanced antidiabetic activity
, India, , ,

合成路线:1 步

参考文献:
A process for the preparation of substituted phenyl ether compounds and rosiglitazone
, World Intellectual Property Organization, , ,

合成路线:1 步

参考文献:
Structural studies on the impurities of troglitazone
Moses Babu, J.; Nageshwar, D.; Ravindra Kumar, Y.; Prabhakar, C.; Sarma, M. R.; et al, Journal of Pharmaceutical and Biomedical Analysis, 2003, 31(2), 271-281

合成路线:1 步

参考文献:
Synthesis of a new antidiabetic medicine 5-[4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]-benzyl]-2,4-thiazolidinedione
Wang, Ensi; Duan, Haifeng; Jin, Lei, Jilin Daxue Ziran Kexue Xuebao, 1999, (4), 85-90
相关文献
化合物详情(旧版)

SMILES

O=C1SC(CC2=CC=C(C=C2)OCC3(C)OC4=C(CC3)C(C)=C(O)C(C)=C4C)C(=O)N1

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