2-ethoxycarbonylamino-3-ethoxycarbonyl-5,6,7,8-tetrahydrobenzo[b]thiophene | 62349-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-ethoxycarbonylamino-3-ethoxycarbonyl-5,6,7,8-tetrahydrobenzo[b]thiophene
• 英文别名: ethyl 2-ethoxycarbonylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylate；2-ethoxycarbonylamino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester；Ethyl 2-(ethoxycarbonylamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
• CAS: 62349-07-9
• 化学式: C₁₄H₁₉NO₄S
• 分子量: 297.375
• InChiKey: VEEPAGJZCIEIJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-ethoxycarbonylamino-3-ethoxycarbonyl-5,6,7,8-tetrahydrobenzo[b]thiophene 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 2-[3-[(4-Methylphenyl)methyl]-2,4-dioxo-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-1-yl]acetic acid
  参考文献：
  名称：

  Syntheses of substituted 2,4-dioxo-thienopyrimidin-1-acetic acids and their evaluation as aldose reductase inhibitors

  摘要：

  A series of 2,4-dioxo-thieno[2,3-d], [3,2-d] and [3,4-d]pyrimidin-1-acetic acids (2) with a benzyl moiety at the N-3 position were prepared and tested in vitro for aldose reductase inhibitory activity against partially purified enzyme from rat lens. Some of these compounds were also evaluated for inhibition of sorbitol accumulation in the sciatic nerve or lens of streptozotocin-induced diabetic rats in vivo. Among the synthesized compounds, several showed potent aldose reductase inhibitory activity with IC50s in the 10(-8) M range. Particularly, the potencies of non-substituted thieno- (2a and 2aa), 5-methylthieno- (2c), 5,6-dimethylthieno-(2g), 6-isopropylthieno- (2j and 2k), 6-chlorothienopyrimidine (2q) and benzothienopyrimidine (2ac) analogs were approximately equipotent to FK-366 (1A) and Ponalrestat (1B) as references. Although most compounds were inactive in vivo, 2 compounds, 2k and 2q, possessed moderate in vivo activity.

  DOI：

  10.1016/0223-5234(93)90112-r
• 作为产物：
  描述：

  2-氨基-4,5,6,7-四氢苯并噻酚-3-羧酸乙酯 、 氯甲酸乙酯 反应 3.0h， 以87%的产率得到2-ethoxycarbonylamino-3-ethoxycarbonyl-5,6,7,8-tetrahydrobenzo[b]thiophene
  参考文献：
  名称：

  Synthesis of Some Thienopyrimidine Derivatives

  摘要：

  硫代噻吩嘧啶酮、烷硫基和芳烷硫噻吩嘧啶酮、噻吩嘧啶酮、噻吩嘧啶、噻吩嘧啶二酮及噻吩三唑嘧啶酮通过2-氨基-3-羧乙氧基-4,5-二取代噻吩和2-氨基-3-氰基-4,5-二取代噻吩与不同试剂的反应制备得到。

  DOI：

  10.3390/11070498

文献信息

• 3-Amino-thieno- und -[1]benzothieno[2,3-d]pyrimidin-derivate
  作者：Fritz Sauter、Peter Stanetty、Hans Potužak

  DOI：10.1002/ardp.19763091109

  日期：——

  In 2‐Stellung basisch substituierte Derivate des 3‐Amino‐thieno[2,3‐d]pyrimidin‐4(3H)‐ons (allg. Formel I) sowie des 3‐Amino‐5.6.7.8‐tetrahydro‐[1]benzothieno[2,3‐d]pyrimidin‐4(3H)‐ons (allg. Formel II) wurden dadurch synthetisiert, daß die entsprechend substituierten 2‐Acylamino‐thiophen‐ (bzw. ‐benzo[b]thiophen‐) carbonsäureester 1a–1o hergestellt und diese mittels Hydrazin in einer einstufigen Reaktion

  3-氨基-噻吩并[2,3-d]嘧啶-4(3H)-one（通式I）和3-氨基-5.6.7.8-四氢-[1]苯并噻吩的衍生物在2-中具有碱性取代基[2,3-d] 嘧啶-4 (3H) -ones（通式II）是通过相应取代的2-酰氨基-噻吩-（或-苯并[b]噻吩-）羧酸酯1a合成的– 1o 和这些在一步反应中使用肼进行取代和环化，得到目标化合物。
• Ogawva K., Yamawaki I., Matsusita Y. I., Nomura N., Kador P. F., Kinoshit+, Eur. I. Med. Chem, 28 (1993) N 10, S 769-781
  作者：Ogawva K., Yamawaki I., Matsusita Y. I., Nomura N., Kador P. F., Kinoshit+

  DOI：——

  日期：——
• Synthesis of Some Thienopyrimidine Derivatives
  作者：Fatma El-Baih、Hanan Al-Blowy、Hassan Al-Hazimi

  DOI：10.3390/11070498

  日期：——

  Thioxothienopyrimidinones, alkylthio- and arylalkylthiothienopyrimidinones, thienopyrimidinones, thienopyrimidines a thienopyrimidinedione and a thienotriazolo- pyrimidinone were prepared from 2-amino-3-carboethoxy-4,5-disubstituted thiophenes and 2-amino-3-cyano-4,5-disubstituted thiophenes via reactions with different reagents.

  硫代噻吩嘧啶酮、烷硫基和芳烷硫噻吩嘧啶酮、噻吩嘧啶酮、噻吩嘧啶、噻吩嘧啶二酮及噻吩三唑嘧啶酮通过2-氨基-3-羧乙氧基-4,5-二取代噻吩和2-氨基-3-氰基-4,5-二取代噻吩与不同试剂的反应制备得到。
• Syntheses of substituted 2,4-dioxo-thienopyrimidin-1-acetic acids and their evaluation as aldose reductase inhibitors
  作者：K Ogawva、I Yamawaki、YI Matsusita、N Nomura、PF Kador、JH Kinoshita

  DOI：10.1016/0223-5234(93)90112-r

  日期：1993.1

  A series of 2,4-dioxo-thieno[2,3-d], [3,2-d] and [3,4-d]pyrimidin-1-acetic acids (2) with a benzyl moiety at the N-3 position were prepared and tested in vitro for aldose reductase inhibitory activity against partially purified enzyme from rat lens. Some of these compounds were also evaluated for inhibition of sorbitol accumulation in the sciatic nerve or lens of streptozotocin-induced diabetic rats in vivo. Among the synthesized compounds, several showed potent aldose reductase inhibitory activity with IC50s in the 10(-8) M range. Particularly, the potencies of non-substituted thieno- (2a and 2aa), 5-methylthieno- (2c), 5,6-dimethylthieno-(2g), 6-isopropylthieno- (2j and 2k), 6-chlorothienopyrimidine (2q) and benzothienopyrimidine (2ac) analogs were approximately equipotent to FK-366 (1A) and Ponalrestat (1B) as references. Although most compounds were inactive in vivo, 2 compounds, 2k and 2q, possessed moderate in vivo activity.