[1,2,3]噻二唑-5-羧酸乙酯 | 4100-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: [1,2,3]噻二唑-5-羧酸乙酯
• 中文别名: 1,2,3-噻二唑-5-羧酸乙酯
• 英文名称: [1,2,3]thiadiazole-5-carboxylic acid ethyl ester
• 英文别名: 1,2,3-thiadiazole-5-carboxylic acid ethyl ester；ethyl 1,2,3-thiadiazole-5-carboxylate；1,2,3-thiadiazol-5-carboxylic acid ethyl ester；1,2,3-Thiadiazol-5-carbonsaeure-ethylester；1,2,3-Thiadiazol-5-carbonsaeureethylester；Ethyl-1,2,3-thiadiazol-5-carboxylat；ethyl thiadiazole-5-carboxylate
• CAS: 4100-14-5
• 化学式: C₅H₆N₂O₂S
• mdl: MFCD00971933
• 分子量: 158.181
• InChiKey: IVZZCUPPIUETNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  [1,2,3]噻二唑-5-羧酸乙酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 1,2,3-噻二唑-5-甲酰肼
  参考文献：
  名称：

  962.吡啶-4-羧酰肼的同类物。第二部分 1,2,3-噻二唑的衍生物

  摘要：

  DOI：

  10.1039/jr9650005166
• 作为产物：
  描述：

  3-氧代丙酸乙酯 在 氯化亚砜 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 生成 [1,2,3]噻二唑-5-羧酸乙酯
  参考文献：
  名称：

  1,2,3-Thiadiazole substituted pyrazolones as potent KDR/VEGFR-2 kinase inhibitors

  摘要：

  KDR kinase inhibition is considered to play an important role in regulating angiogenesis, which is vital for the survival and proliferation of tumor cells. Recently we disclosed a structure-based kinase inhibitor design strategy which led to the identification of a new class of VEGFR-2/KDR kinase inhibitors bearing heterocyclic substituted pyrazolones as the core template. Instability in a rat S9 preparation and poor iv PK profiles for most of these inhibitors necessitated exploration of new pyrazolones to identify new analogs with improved metabolic stability. Optimization of the heterocyclic moiety led to the identification of the thiadiazole series of pyrazolones (D) as potent VEGFR-2/KDR kinase inhibitors. SAR modifications, kinase selectivity profiling, and structural elements for improved PK properties were explored. Oral bioavailability up to 29% was achieved in the rat. Modeling results based on the Glide XP docking approach supported our postulation regarding the interaction of the lactam segment of the pyrazolones with the hinge region of the KDR kinase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.054

文献信息

• Method of treating a patient having precancerous lesions with quinazoline derivatives
  申请人：Cell Pathways, Inc.

  公开号：US06262059B1

  公开（公告）日：2001-07-17

  Derivatives of Quinazoline are useful for the treatment of patients having precancerous lesions. These compounds are also useful to inhibit growth of neoplastic cells.

  喹唑啉衍生物对于治疗患有癌前病变的患者很有用。这些化合物还可用于抑制肿瘤细胞的生长。
• The reaction of 1,2,3-thiadiazoles with base. I. A new route to 1-alkynyl thioethers
  作者：R. Raap、R. G. Micetich

  DOI：10.1139/v68-179

  日期：1968.4.1

  unsubstituted in the 5-position, and a strong base such as an organolithium compound, sodamide, sodium methylsulfinyl carbanion, or potassium t-butoxide results in cleavage of the thiadiazole ring system with evolution of nitrogen and formation of alkalimetal alkynethiolate. Subsequent addition of an alkyl or acyl halide to the reaction mixture produces 1-alkynyl thioethers. 4-(5-Phenyl-1,2,3-thiadiazolyl)lithium

  5-位未取代的 1,2,3-噻二唑与强碱（如有机锂化合物、钠酰胺、甲基亚磺酰基碳负离子钠或叔丁醇钾）之间的反应导致噻二唑环系统裂解，并产生氮和碱金属炔硫醇盐的形成。随后向反应混合物中加入烷基卤或酰基卤产生1-炔基硫醚。4-(5-苯基-1,2,3-噻二唑基)锂，由5-苯基-1,2,3-噻二唑和甲基-或苯基锂得到，与甲基碘反应生成4-甲基-5-苯基- 1,2,3-噻二唑。
• 1,2,3-Thiadiazole amides
  申请人：Bristol-Myers Company

  公开号：US04101548A1

  公开（公告）日：1978-07-18

  A series of novel 4-amino-2-(thiadiazole-carbonyl piperazinyl)-6,7-dimethoxyquinazolines is disclosed having antihypertensive properties. The thiadiazole substituent may be optionally substituted with alkyl or lower alkoxy carbonylamino groups. A representative embodiment of the invention is 4-amino-6,7-dimethoxy-2-[4-(5-ethoxy-carbonylamino-1,2,3-thiadiazole-4-car bonyl)-piperazin-1-yl]-quinazoline.

  披露了一系列具有降压作用的新型4-氨基-2-(噻二唑-羰基哌嗪基)-6,7-二甲氧基喹唑啉化合物。噻二唑取代基可以选择性地被烷基或较低的烷氧羰胺基所取代。该发明的代表性实施形式是4-氨基-6,7-二甲氧基-2-[4-(5-乙氧基羰胺基-1,2,3-噻二唑-4-羰基)-哌嗪-1-基]-喹唑啉。
• Selenium heterocycles XVIII: Synthesis and antibacterial activity of 4‐substituted (1,2,3‐selenadiazol‐5‐yl)carbamic acid esters and their sulfur analogs
  作者：A. Shafiee、I. Lalezari、S. Yazdani、F.M. Shahbazian、T. Partovi

  DOI：10.1002/jps.2600650234

  日期：1976.2

  4-Substituted (1,2,3-selenadiazol-5-yl)carbamic acid esters and their sulfur analogs were prepared from the Curtius rearrangement of the corresponding carboxazides. None of the compounds showed significant antibacterial activity.

  由相应的羧叠氮化物的库尔修斯（Curtius）重排制备4-取代的（1,2,3-硒二氮杂-5-基）氨基甲酸酯及其硫类似物。这些化合物均未显示出显着的抗菌活性。
• 1,2,3-Thiadiazole process
  申请人：Bristol-Myers Company

  公开号：US04171363A1

  公开（公告）日：1979-10-16

  A series of novel 4-amino-2-(thiadiazole-carbonyl piperazinyl)-6,7-dimethoxyquinazolines is disclosed having antihypertensive properties. The thiadiazole substituent may be optionally substituted with alkyl or lower alkoxy carbonylamino groups. A representative embodiment of the invention is 4-amino-6,7-dimethoxy-2-[4-(5-ethoxy-carbonylamino-1,2,3-thiadiazole-4-car bonyl)-piperazin-1-yl]-quinazoline.

  本发明揭示了一系列新型4-氨基-2-(噻二唑-羰基哌嗪基)-6,7-二甲氧基喹唑啉，具有降压作用。噻二唑取代基可以选择性地用烷基或较低的烷氧羰基氨基基团取代。本发明的代表实施例是4-氨基-6,7-二甲氧基-2-[4-(5-乙氧羰基氨基-1,2,3-噻二唑-4-羰基)-哌嗪-1-基]-喹唑啉。