2-氨基-5-甲基噻吩-3-羧酸叔丁酯 | 59713-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-氨基-5-甲基噻吩-3-羧酸叔丁酯
• 英文名称: tert-butyl 2-amino-5-methylthiophene-3-carboxylate
• CAS: 59713-53-0
• 化学式: C₁₀H₁₅NO₂S
• 分子量: 213.301
• InChiKey: FHVXMCVYRAHXOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-5-甲基噻吩-3-羧酸叔丁酯 、 己二酰氯 以 N,N-二甲基乙酰胺 为溶剂， 以77%的产率得到di-tert-butyl 2,2'-[(1,6-dioxohexane-1,6-diyl)diimino]bis(5-methylthiophene-3-carboxylate)
  参考文献：
  名称：

  Structure-Activity Relationships of New 2-Acylamino-3-thiophenecarboxylic Acid Dimers as Plasminogen Activator Inhibitor-1 Inhibitors

  摘要：

  迄今为止，纤溶酶原激活物抑制剂（PAI）-1 的小分子抑制剂已有报道，但其临床效果仍然未知。本研究以 TM5001 (1) 和 TM5007 (2) 的核心结构为基础，研究了新合成的 2-酰氨基-3-噻吩羧酸二聚体的结构-活性关系（SAR）。一般来说，在两个噻吩环上都具有笨重或/和疏水取代基（如苯基、异丁基）的化合物，无论取代基的位置如何，都具有很强的 PAI-1 抑制活性。单羧基衍生物（10）对 PAI-1 的抑制作用与相应的二羧基化合物（9f）相当。

  DOI：

  10.1248/cpb.58.615

文献信息

• Pancreatic lipase inhibitor compounds, their synthesis and use
  申请人：——

  公开号：US20030195199A1

  公开（公告）日：2003-10-16

  The subject invention features compounds having the structure: 1 wherein X is O, S, CH 2 or NR 5 ; Y is O or S; R 1 is H, substituted or unsubstituted C 1 -C 15 alkyl, C 1 -C 8 alkylaryl, —C(O)OR 4 , —C(O)NR 4 R 5 , —CR 6 R 6′ OR 4 , —CR 6 R 6′ OC(O)R 4 , —CR 6 R 6′ OC(O)NHR 7 , —C(O)NR 10 R 11 , —C(O)NR 8 R 9 NR 8 R 9 , —N(R 5 )C(O)NHR 5 , or CH 2 R 4 ; R 2 is a substituted or unsubstituted, straight chain C 1 —C 30 alkyl or branched C 3 -C 30 alkyl, aryl, alkylaryl, arylalkyl, heteroarylalkyl or cycloalkyl; R 3 is H or substituted or unsubstituted C 1 -C 6 alkyl or C 3 -C 10 cycloalkyl; R 4 is H or a substituted or unsubstituted, straight chain or branched, C 6 -C 30 alkyl, aryl, —CH 2 -aryl, aryl —C 1 -C 15 alkyl, heteroaryl-C 1 -C 15 alkyl or C 3 -C 10 cycloalkyl; R 5 is H or a substituted or unsubstituted, straight chain or branched, C 6 -C 30 alkyl, aryl C 1 -C 30 alkyl, heteroarylalkyl or cycloalkyl; R 6 and R 6′ are each independently H, substituted or unsubstituted C 1 -C 6 alkyl, dialkyl or C 3 -C 10 cycloalkyl or together form a 3-7 membered ring system; R 7 is H or substituted or unsubstituted C 1 -C 12 alkyl or C 3 -C 10 cycloalkyl; R 8 and R 9 are each independently H, substituted or unsubstituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylaryl, or NR 8 R 9 together form a substituted piperazine or piperidine ring or a dihydro-1H-isoquinoline ring system, or a specific enantiomer thereof, or a specific tautomer, or a pharmaceutically acceptable salt thereof and a method for treating diabetes or obesity by administering a therapeutically effective amount of the compounds of the invention.

  该发明涉及具有以下结构的化合物：1其中X为O、S、CH2或NR5；Y为O或S；R1为H、取代或未取代的C1-C15烷基、C1-C8烷基芳基、—C（O）OR4、—C（O）NR4R5、—CR6R6′OR4、—CR6R6′OC（O）R4、—CR6R6′OC（O）NHR7、—C（O）NR10R11、—C（O）NR8R9NR8R9、—N（R5）C（O）NHR5或CH2R4；R2为取代或未取代的、直链C1-C30烷基或支链C3-C30烷基、芳基、烷基芳基、芳基烷基、杂环芳基烷基或环烷基；R3为H或取代或未取代的C1-C6烷基或C3-C10环烷基；R4为H或取代或未取代的、直链或支链的C6-C30烷基、芳基、—CH2-芳基、芳基—C1-C15烷基、杂环芳基-C1-C15烷基或C3-C10环烷基；R5为H或取代或未取代的、直链或支链的C6-C30烷基、芳基C1-C30烷基、杂环芳基烷基或环烷基；R6和R6'各自独立地为H、取代或未取代的C1-C6烷基、二烷基或C3-C10环烷基，或者共同形成一个3-7成员环系统；R7为H或取代或未取代的C1-C12烷基或C3-C10环烷基；R8和R9各自独立地为H、取代或未取代的C1-C6烷基、C1-C6烷氧基、C1-C6烷基芳基或NR8R9，共同形成取代的哌嗪或哌啶环或二氢-1H-异喹啉环系统，或其特定对映体，或其特定互变异构体，或其药学上可接受的盐，并通过给予该发明化合物的治疗有效剂量来治疗糖尿病或肥胖症的方法。
• Thieno-(1,3)-oxazin-4-ones with lipase inhibiting activity
  申请人：Hodson Francis Harold

  公开号：US20050075336A1

  公开（公告）日：2005-04-07

  The use of a compound comprising formula (I), or a salt, ester, amide or prodrug thereof in the treatment of obesity and related disorders. The invention also relates to novel compounds within formula (I), to processes for preparing them and pharmaceutical compositions containing them. In formula (I): A is an optionally substituted thienyl moiety, Y is O, S, or NR 2 , R 1 is a branched or unbranched alkyl (optionally interrupted by one or more oxygen atoms), alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, arylalkyl, reduced arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, reduced aryl, reduced heteroaryl, reduced heteroarylalkyl or a substituted derivative of any of the foregoing groups and R 2 is hydrogen or a group as defined for R 1 .

  使用具有式（I）的化合物，或其盐，酯，酰胺或前药治疗肥胖症及相关疾病。本发明还涉及公式（I）内的新化合物，制备它们的方法以及含有它们的制药组合物。在公式（I）中：A是可选择取代的噻吩基团，Y是O，S或NR2，R1是支链或非支链烷基（可被一个或多个氧原子中断），烯基，炔基，环烷基，环烷烯基，芳基，芳基烷基，还原芳基烷基，芳基烯基，杂环芳基，杂环芳基烷基，还原杂环芳基，还原杂环芳基烷基或任何上述基团的取代衍生物，R2是氢或与R1定义相同的基团。
• Glycogen Phosphorylase Inhibitor Compounds and Pharmaceutical Compositions Thereof
  申请人：Evans Karen

  公开号：US20070249670A1

  公开（公告）日：2007-10-25

  The invention relates to glycogen phosphorylase inhibitor compounds, pharmaceutical compositions of these compounds, methods of treatment using the pharmaceutical compositions to treat diabetes, conditions associated with diabetes, and/or tissue ischemia, including myocardial ischemia, and processes for making the compounds.

  本发明涉及糖原磷酸化酶抑制剂化合物、这些化合物的药物组合物、使用这些药物组合物治疗糖尿病、与糖尿病相关的疾病和/或组织缺血，包括心肌缺血的方法，以及制备这些化合物的过程。
• THIENO-(1,3)-OXAZIN-4-ONES WITH LIPASE INHIBITING ACTIVITY
  申请人：HODSON Harold Francis

  公开号：US20090029978A1

  公开（公告）日：2009-01-29

  The use of a compound comprising formula (I), or a salt, ester, amide or prodrug thereof in the treatment of obesity and related disorders. The invention also relates to novel compounds within formula (I), to processes for preparing them and pharmaceutical compositions containing them. In formula (I): A is an optionally substituted thienyl moiety, Y is O, S, or NR 2 , R 1 is a branched or unbranched alkyl (optionally interrupted by one or more oxygen atoms), alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, arylalkyl, reduced arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, reduced aryl, reduced heteroaryl, reduced heteroarylalkyl or a substituted derivative of any of the foregoing groups and R 2 is hydrogen or a group as defined for R 1 .

  使用公式（I）或其盐，酯，酰胺或前药治疗肥胖症及相关疾病。本发明还涉及公式（I）内的新化合物，制备它们的过程以及含有它们的制药组合物。在公式（I）中：A是可选择取代的噻吩基团，Y是O，S或NR2，R1是支链或直链烷基（可被一个或多个氧原子中断），烯基，炔基，环烷基，环烷烯基，芳基，芳基烷基，还原芳基烷基，芳基烯基，杂环芳基，杂环芳基烷基，还原杂环芳基，还原杂环芳基烷基或任何上述基团的取代衍生物，R2是氢或与R1定义相同的基团。
• PANCREATIC LIPASE INHIBITOR COMPOUNDS, THEIR SYNTHESIS AND USE
  申请人：OSI Pharmaceuticals, Inc.

  公开号：EP1467978A1

  公开（公告）日：2004-10-20