5-溴噻唑烷-2,4-二酮 | 125518-48-1

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-溴噻唑烷-2,4-二酮
• 英文名称: 5-bromo-thiazolidine-2,4-dione
• 英文别名: 5-Bromothiazolidine-2,4-dione；5-bromo-1,3-thiazolidine-2,4-dione
• CAS: 125518-48-1
• 化学式: C₃H₂BrNO₂S
• 分子量: 196.024
• InChiKey: KRBBGMOONSUDGO-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对氟苯硫酚 、 5-溴噻唑烷-2,4-二酮 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 16.0h， 以75%的产率得到5-(4-fluorophenylsulfanyl)-thiazolidine-2,4-dione
  参考文献：
  名称：

  Novel 5-(3-Aryl-2-propynyl)-5-(arylsulfonyl)thiazolidine-2,4-diones as Antihyperglycemic Agents

  摘要：

  Novel 5-(3-aryl-2-propynyl)-5-(arylsulfonyl)th and 5-(3-aryl-2-propynyl)5-(arylsulfonyl)thiazolidine-2,4-diones were prepared and evaluated as oral antihyperglycemic agents in the obese, insulin resistant db/db mouse model at 100 mg/kg and, if the analogue had sufficient potency, 20 mg/kg. The sulfonylthiazolidinediones, 2, were more potent than the corresponding sulfanylthiazolidinedione congeners, 1. With regard to substituent effects on the 3-propynyl phenyl ring (Ar') of 2,4-halogen, substitution generally resulted in the more potent analogues. Substituent effects on the phenylsulfonyl moiety (Ar) of 2 were less clear, although para-halogen substitution on Ar generally was preferable. 2-Pyridinesulfonyl derivatives (Ar = 2-pyridine in 2) also had good potency. Several compounds from series 2 were effective at lowering glucose and insulin in the obese, insulin resistant ob/ob mouse at the 50 mg/kg oral dose. Compound 20 significantly improved the glucose tolerance of obese, insulin resistant Zucker rats at the 20 mg/kg dose level and had no effect on plasma glucose or on glucose tolerance in normal rats fasted for 18 h at the 100 mg/kg level.

  DOI：

  10.1021/jm9706168
• 作为产物：
  描述：

  2,4-噻唑烷二酮 在 溴 作用下， 以 溶剂黄146 为溶剂， 以56.7%的产率得到5-溴噻唑烷-2,4-二酮
  参考文献：
  名称：

  5-[(1- and 2-naphthalenyl) sulfonyl]-2,4-thiazolidinediones and

  摘要：

  本文披露了公式I和II的1-或2-硫、硫亚甲基和磺酰基萘衍生物，或其药用可接受的阳离子盐，其中n为0或1，R.sub.5为氢、溴、氯、三氟甲基或二氟乙基；R.sub.6为氢、羟基、甲氧基或乙氧基；R.sub.7为氢或R.sub.7和R.sub.6都是甲基或乙基碳酸酯，但当S(O).sub.2在萘环的2位置时，R.sub.5、R.sub.6和R.sub.7都是氢。所披露的化合物具有降低血糖作用，并可用于治疗糖尿病。

  公开号：

  US04997948A1

文献信息

• [EN] CRBN LIGANDS AND USES THEREOF<br/>[FR] LIGANDS CRBN ET LEURS UTILISATIONS
  申请人：KYMERA THERAPEUTICS INC

  公开号：WO2019140387A1

  公开（公告）日：2019-07-18

  The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.

  本发明提供了化合物、其组合物以及使用这些化合物抑制CRBN并治疗CRBN介导的疾病的方法。
• Azolidines as beta-3 adrenergic receptor agonists
  申请人：American Home Products Corporation

  公开号：US20020032222A1

  公开（公告）日：2002-03-14

  This invention provides compounds of Formula I having the structure 1 wherein, A, X, Y, Z, W, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are as defined hereinbefore or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

  本发明提供了具有以下结构式的I号化合物的药物或药用盐，其中A、X、Y、Z、W、R1、R2、R3、R4、R5和R6的定义如前所述。这些化合物可用于治疗或抑制与胰岛素抵抗或高血糖（通常与肥胖或葡萄糖不耐受有关）相关的代谢紊乱、动脉粥样硬化、胃肠疾病、神经源性炎症、青光眼、眼压增高和频繁排尿，特别是在治疗或抑制2型糖尿病方面特别有用。
• [EN] DIAZENIUMDIOLATE HETEROCYCLIC DERIVATIVES<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES DE DIAZÉNIUMDIOLATE
  申请人：MERCK SHARP & DOHME

  公开号：WO2012058203A1

  公开（公告）日：2012-05-03

  A compound having the structure: useful for treating hypertension, Pulmonary Arterial Hypertension (PAH), congestive heart failure, conditions resulting from excessive water retention, cardiovascular disease, diabetes, oxidative stress, endothelial dysfunction, cirrhosis, pre-eclampsia, osteoporosis or nephropathy.

  一种具有以下结构的化合物：用于治疗高血压、肺动脉高压（PAH）、充血性心力衰竭、由过多水潴留引起的疾病、心血管疾病、糖尿病、氧化应激、内皮功能障碍、肝硬化、子痫前期、骨质疏松症或肾病。
• Certain-[3-aryl-prop-2-ynyl]-5-(arylsulfonyl) thiazolidine -2,4-dione
  申请人：American Home Products Corporation

  公开号：US05574051A1

  公开（公告）日：1996-11-12

  This invention relates to novel 5-[3-aryl-prop-2-ynyl]-5-(arylsulfonyl)- thiazolidine-2,4-diones and 5-[3-aryl-prop-2-ynyl]-5-(arylsulfanyl)thiazolidine-2,4-diones characterized by the general formula (I), seen below, wherein Ar is phenyl, 2-naphthyl, alkyl substituted phenyl, alkoxy substituted phenyl, halogen substituted phenyl, 2-phenyl, substituted 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-quinolinyl, 2-pyrimidinyl, 2-benzoxazolyl, 2-benzthiazolyl, 2-benzimidazolyl, 2-furanyl, 2-benzo-[b]-furanyl, 2-thienyl, 2-benzo-[b]-thienyl; n is 0 or 2; and Ar' is phenyl, alkyl substituted phenyl, perfluoroalkyl substituted phenyl, halogen substituted phenyl, alkoxy substituted phenyl, perfluoroalkoxy substituted phenyl and alkylio substituted phenyl. ##STR1## This invention also relates to the use of the abovementioned compounds in lowering the blood glucose levels in hyperglycemic mammals and pharmaceutical compositions containing the same.

  这项发明涉及新颖的5-[3-芳基-丙-2-炔基]-5-(芳基磺酰基)-噻唑烷-2,4-二酮和5-[3-芳基-丙-2-炔基]-5-(芳基硫基)噻唑烷-2,4-二酮，其具有下面的通用式(I)所示的特征，其中Ar是苯基、2-萘基、烷基取代苯基、烷氧基取代苯基、卤素取代苯基、2-苯基、取代的2-吡啶基、3-吡啶基、4-吡啶基、2-喹啉基、2-嘧啶基、2-苯并噁唑基、2-苯并噻唑基、2-苯并咪唑基、2-呋喃基、2-苯并[ b ]-呋喃基、2-噻吩基、2-苯并[ b ]-噻吩基；n为0或2；Ar'为苯基、烷基取代苯基、全氟烷基取代苯基、卤素取代苯基、烷氧基取代苯基、全氟烷氧基取代苯基和烷氧基取代苯基。该发明还涉及上述化合物在降低高血糖哺乳动物的血糖水平以及含有这些化合物的药物组合物的用途。
• Amino-thiazolidinediones useful in the treatment of insulin resistance and hyperglycemia
  申请人：——

  公开号：US06214842B1

  公开（公告）日：2001-04-10

  This invention provides compounds of Formula I having the structure wherein: R is hydrogen or alkyl of 1-6 carbon atoms; A is R1, R2, R3 are each, independently, hydrogen, alkoxy of 1-6 carbon atoms, thioalkyl of 1-6 carbon atoms, trifluoromethyl, R4 is hydrogen, alkyl of 1-6 carbon atoms, halogen, or alkoxy of 1-6 carbon atoms; R5 is phenyl, naphthyl, thienyl, furyl, wherein R5 may be optionally mono-, di-, or tri-substituted with a sustituent selected from the group consisting of alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, trifluoromethyl, halogen, alkoxycarbonyl of 2-7 carbon atoms, alkylamino of 1-6 carbon atoms, and dialkylamino in which each of the alkyl groups is of 1-6 carbon atoms, nitro, cyano, —CO2H, alkylcarbonyloxy of 2-7 carbon atoms, and alkylcarbonyl of 2-7 carbon atoms; m=1-4; n=1-4; and X=O, S, or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

  该发明提供了具有结构的化合物I，其中：R为氢或1-6个碳原子的烷基；A为R1，R2，R3分别独立地为氢，1-6个碳原子的烷氧基，1-6个碳原子的硫代烷基，三氟甲基，R4为氢，1-6个碳原子的烷基，卤素或1-6个碳原子的烷氧基；R5为苯基，萘基，噻吩基，呋喃基，其中R5可以选择性地单取代，二取代或三取代，取代基选自1-6个碳原子的烷基，1-6个碳原子的烷氧基，三氟甲基，卤素，2-7个碳原子的烷氧羰基，1-6个碳原子的烷基氨基和两个烷基均为1-6个碳原子，硝基，氰基，-CO2H，2-7个碳原子的烷基羧氧基和2-7个碳原子的烷基羰基；m=1-4；n=1-4；X=O，S，或其药用盐，这些化合物在治疗与胰岛素抵抗或高血糖相关的代谢紊乱方面具有用途。