7-methoxy-4-<2-(N,N-dipropylamino)ethyl>isatin | 108773-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-methoxy-4-<2-(N,N-dipropylamino)ethyl>isatin
• 英文别名: 4-[2-(dipropylamino)ethyl]-7-methoxy-1H-indole-2,3-dione
• CAS: 108773-27-9
• 化学式: C₁₇H₂₄N₂O₃
• 分子量: 304.389
• InChiKey: BSJAKRHWVRAQBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-4-<2-(N,N-dipropylamino)ethyl>isatin 在 氢溴酸 作用下， 反应 7.0h， 以52%的产率得到7-hydroxy-4-<2-(N,N-dipropylamino)ethyl>isatin hydrobromide
  参考文献：
  名称：

  Synthesis and evaluation of non-catechol D-1 and D-2 dopamine receptor agonists: benzimidazol-2-one, benzoxazol-2-one, and the highly potent: benzothiazol-2-one 7-ethylamines

  摘要：

  Our interest in identifying D-1 and D-2 dopamine receptor agonists that are not catechols led us to extend previous studies with oxindoles by investigating analogues of dopamine, N,N-dipropyldopamine, m-tyramine, N,N-dipropyl-m-tyramine, and epinine in which the m-hydroxyl is replaced by the NH portion of a thiazol-2-one, oxazol-2-one, or imidazol-2-one group fused to the 2,3-position. These compounds were evaluated for their affinity and agonist activity at D-1 and D-2 receptors by using in vitro assays. Replacement of the m-hydroxy in N,N-dipropyldopamine with the thiazol-2-one group resulted in a dramatic increase in D-2 receptor affinity and activity compared to that of N,N-dipropyldopamine itself or that of the corresponding oxindole, 1. The resulting compound, 7-hydroxy-4-[2-(di-n-propylamino)ethyl]benzothiazol-2(3H)-one (4), is the most potent D-2 receptor agonist reported to date in the field-stimulated rabbit ear artery (ED50 = 0.028 nM). The benzoxazol-2-one (6), benzimidazol-2-one (5), and isatin (51) analogues showed D-2 receptor agonist potency similar to that of 1. The des-7-hydroxyl analogue of 4 (21) also has enhanced D-2 receptor activity compared to that of the corresponding oxindole, 8. 7-Hydroxy-4-(2-aminoethyl)benzothiazol-2(3H)-one, 27, a non-catechol, has enhanced D-1 and D-2 receptor activity in vitro compared to that of the corresponding oxindole, 7. In vivo, 27 increased renal blood flow and decreased blood pressure in the dog. However, these effects were mediated primarily by D-2 receptor agonist activity. This may be a result of the D-1 partial agonist activity of 27 coupled with its potent D-2 receptor activity.

  DOI：

  10.1021/jm00390a009
• 作为产物：
  描述：

  (2E)-N-[5-[2-(dipropylamino)ethyl]-2-methoxyphenyl]-2-hydroxyiminoacetamide 生成 7-methoxy-4-<2-(N,N-dipropylamino)ethyl>isatin
  参考文献：
  名称：

  STRINGER, O. D.;WEINSTOCK, J.;WILSON, J. W.

  摘要：

  DOI：

文献信息

• STRINGER, O. D.;WEINSTOCK, J.;WILSON, J. W.
  作者：STRINGER, O. D.、WEINSTOCK, J.、WILSON, J. W.

  DOI：——

  日期：——
• WEINSTOCK J.;GAITONOPOULOS D. E.;STRINGER O. D.;WILLIAM A., J. MED. CHEM., 1987, 30, N 7, 1166-1176
  作者：WEINSTOCK J.、GAITONOPOULOS D. E.、STRINGER O. D.、WILLIAM A.

  DOI：——

  日期：——
• Synthesis and evaluation of non-catechol D-1 and D-2 dopamine receptor agonists: benzimidazol-2-one, benzoxazol-2-one, and the highly potent: benzothiazol-2-one 7-ethylamines
  作者：Joseph Weinstock、Dimitri E. Gaitanopoulos、Orum D. Stringer、Robert G. Franz、J. Paul Hieble、Lewis B. Kinter、William A. Mann、Kathryn E. Flaim、George Gessner

  DOI：10.1021/jm00390a009

  日期：1987.7

  Our interest in identifying D-1 and D-2 dopamine receptor agonists that are not catechols led us to extend previous studies with oxindoles by investigating analogues of dopamine, N,N-dipropyldopamine, m-tyramine, N,N-dipropyl-m-tyramine, and epinine in which the m-hydroxyl is replaced by the NH portion of a thiazol-2-one, oxazol-2-one, or imidazol-2-one group fused to the 2,3-position. These compounds were evaluated for their affinity and agonist activity at D-1 and D-2 receptors by using in vitro assays. Replacement of the m-hydroxy in N,N-dipropyldopamine with the thiazol-2-one group resulted in a dramatic increase in D-2 receptor affinity and activity compared to that of N,N-dipropyldopamine itself or that of the corresponding oxindole, 1. The resulting compound, 7-hydroxy-4-[2-(di-n-propylamino)ethyl]benzothiazol-2(3H)-one (4), is the most potent D-2 receptor agonist reported to date in the field-stimulated rabbit ear artery (ED50 = 0.028 nM). The benzoxazol-2-one (6), benzimidazol-2-one (5), and isatin (51) analogues showed D-2 receptor agonist potency similar to that of 1. The des-7-hydroxyl analogue of 4 (21) also has enhanced D-2 receptor activity compared to that of the corresponding oxindole, 8. 7-Hydroxy-4-(2-aminoethyl)benzothiazol-2(3H)-one, 27, a non-catechol, has enhanced D-1 and D-2 receptor activity in vitro compared to that of the corresponding oxindole, 7. In vivo, 27 increased renal blood flow and decreased blood pressure in the dog. However, these effects were mediated primarily by D-2 receptor agonist activity. This may be a result of the D-1 partial agonist activity of 27 coupled with its potent D-2 receptor activity.