4-methoxy-7-<2-(N,N-dipropylamino)ethyl>benzimidazol-2(3H)-one | 101389-63-3

• 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: 4-methoxy-7-<2-(N,N-dipropylamino)ethyl>benzimidazol-2(3H)-one
• 英文别名: 7-methoxy-4-[2-(N,N-dipropylamino)ethyl]-2,3-dihydro-2-benzimidazolone；4-[2-(dipropylamino)ethyl]-7-methoxy-1,3-dihydrobenzimidazol-2-one
• CAS: 101389-63-3
• 化学式: C₁₆H₂₅N₃O₂
• 分子量: 291.393
• InChiKey: KOOOKVZUVUWRPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxy-7-<2-(N,N-dipropylamino)ethyl>benzimidazol-2(3H)-one 在 三溴化硼 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 4.0h， 以86%的产率得到4-hydroxy-7-<2-(N,N-dipropylamino)ethyl>benzimidazol-2(3H)-one 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：

  3-(benzyloxy)-7-methoxy-4-<2-(N,N-dipropylamino)ethyl>benzimidazol-2(3H)-one acetate 以75%的产率得到
  参考文献：
  名称：

  STRINGER, O. D.;WEINSTOCK, J.

  摘要：

  DOI：

文献信息

• Novel dopamine derivatives, processes for their preparation, and their
  申请人：Schering Aktiengesllschaft

  公开号：US04958026A1

  公开（公告）日：1990-09-18

  The disclosure relates to novel dopamine derivatives of general Formula I ##STR1## wherein A is a substituted phenyl residue of the structure ##STR2## wherein R.sup.1 and R.sup.2, being identical or different, mean hydrogen, C.sub.1-15 -alkyl and allyl, D is ##STR3## R.sub.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, CF.sub.3, NH.sub.2 E is ##STR4## X is OH, NH.sub.2, ##STR5## and NH--SO.sub.2 --CF.sub.3, if Y=OH, Y is OH, NH.sub.2, ##STR6## NH--SO.sub.2 --CF.sub.3 and NH--SO.sub.2 --CH.sub.3, if X=OH, but wherein X and Y do not simultaneously mean OH, with R.sup.3 being C.sub.1-4 -alkyl, and Z is H or OH, and, if Z means the hydroxy group, the residue A can also be present in the tautomeric basic form, and their acid addition salts, their preparation, and use as medicinal agents having antihypertensive activity.

  该披露涉及一般式I的新型多巴胺衍生物，其中A是结构的取代苯基残基，其中R.sup.1和R.sup.2，相同或不同，表示氢，C.sub.1-15-烷基和烯丙基，D是R4是氢，C.sub.1-C.sub.4-烷基，CF.sub.3，NH.sub.2 E是X是OH，NH.sub.2，如果Y=OH，则Y是OH，NH.sub.2，如果X=OH，则X是OH，但X和Y不同时表示OH，其中R.sup.3为C.sub.1-4-烷基，Z为H或OH，如果Z表示羟基，则残基A也可以以互变异构的碱性形式存在，以及它们的酸盐，它们的制备和用作具有降压活性的药用剂。
• ——
  作者：ALBRECHT R.、 SCHOLLKOPF K.、 SCHRODER G.

  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：——
• NEUE DOPAMIN-DERIVATE, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS ARZNEIMITTEL
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0189473A1

  公开（公告）日：1986-08-06
• US4958026A
  申请人：——

  公开号：US4958026A

  公开（公告）日：1990-09-18