2,4-dimethoxybenzothiazole-7-acetonitrile | 108773-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2,4-dimethoxybenzothiazole-7-acetonitrile
• 英文别名: (2,4-dimethoxy-1,3-benzothiazol-7-yl)-acetonitrile；7-acetonitrile-2,4-dimethoxybenzothiazole；[2,4-Dimethoxy-1,3-benzothiazol-7-yl]acetonitrile；2-(2,4-dimethoxy-1,3-benzothiazol-7-yl)acetonitrile
• CAS: 108773-02-0
• 化学式: C₁₁H₁₀N₂O₂S
• 分子量: 234.279
• InChiKey: QWWFXQIXDNEMGW-UHFFFAOYSA-N

物化性质

• 熔点：
  127-129 °C
• 沸点：
  399.0±50.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxybenzothiazole-7-acetonitrile 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 生成 (2,4-Dimethoxy-1,3-benzothiazol-7-yl)acetic acid
  参考文献：
  名称：

  7-(2-aminoethyl) benzothiazolones

  摘要：

  公式I的化合物已被披露，其中Ar代表一个基团，X代表一个C.sub.1-12烷基链，该链可以被--S(O).sub.n --，--O--，--C(Z)--，CR.sup.6 R.sup.7，苯基甲炔，--NR.sup.8 --，--CONH--，--NHCO--和--NHCONH--等一个或多个基团中断或终止，Y代表一个可选择取代的芳基或环烷基基团，Z代表O或S，R.sup.1，R.sup.2，R.sup.5和R.sup.9各自独立地代表氢或烷基C.sub.1-6，R.sup.3和R.sup.4代表氢，或R.sup.3和R.sup.4一起形成一个基团--S--，--NR.sup.9 --或--CH.sub.2--，R.sup.6和R.sup.7独立地代表氢，烷基C.sub.1-6，氟，氰基或CF.sub.3，只要R.sup.6和R.sup.7中至少有一个不是氢，R.sup.8代表氢或烷基C.sub.1-6，或者当X被多个--NR.sup.8 --基团中断或终止时，它们可以与另一个R.sup.8基团一起形成链--CH.sub.2--CH.sub.2--，n代表0，1或2，以及其药学上可接受的衍生物。还描述了它们的生产过程和包含它们使用的治疗方法的药物组合物。

  公开号：

  US05648370A1
• 作为产物：
  描述：

  4-甲氧基-7-甲基苯并噻唑-2-胺 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 磷酸 、 copper(II) sulfate 、 sodium chloride 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 10.73h， 生成 2,4-dimethoxybenzothiazole-7-acetonitrile
  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

文献信息

• Compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity
  申请人：Mammen Mathai

  公开号：US20050113417A1

  公开（公告）日：2005-05-26

  The invention is directed to compounds of formula I: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7a , R 7b , W, G 1 , G 2 , a, b, c, d and m are as defined in the specification, or a pharmaceutically acceptable salt or solvate or stereoisomer thereof. The invention is also directed to pharmaceutical compositions comprising such compounds; methods of using such compounds; and process and intermediates for preparing such compounds.

  这项发明涉及到以下式I的化合物：其中R1、R2、R3、R4、R5、R6、R7a、R7b、W、G1、G2、a、b、c、d和m如规范中所定义，或其药学上可接受的盐、溶剂或立体异构体。该发明还涉及包含这些化合物的药物组合物；使用这些化合物的方法；以及制备这些化合物的过程和中间体。
• 7-(2-aminoethyl)-1,3-Benzthia- or oxa- zol-2(3H) -ones
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0174811A2

  公开（公告）日：1986-03-19

  Compounds of formula (I): O-C2-8-alkanoyl derivatives thereof and pharmaceutically acceptable salts are described in which X is -S- or -0-, R1 and R2 are, each, hydrogen, C1-6-alkyl, allyl, benzyl, phenethyl, methoxyphenethyl or hydroxyphenethyl; and R3 and R4 are, each, hydroxy, hydrogen, halo, C1-3-alkyl or C1-3alkoxy. The compounds are dopamine agonists and have antihypertensive activity. Pharmaceutical compositions and methods of use are described, as are processes for their preparation.

  式(I)化合物： 其中 X 为-S-或-0-，R1 和 R2 分别为氢、C1-6-烷基、烯丙基、苄基、苯乙基、甲氧基苯乙基或羟基苯乙基；R3 和 R4 分别为羟基、氢、卤代、C1-3-烷基或 C1-3 烷氧基。这些化合物是多巴胺激动剂，具有抗高血压活性。本文描述了药物组合物和使用方法，以及其制备工艺。
• 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：——
• BIOLOGICALLY ACTIVE AMINES
  申请人：FISONS plc

  公开号：EP0558677A1

  公开（公告）日：1993-09-08
• COMPOUNDS HAVING BETA2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY
  申请人：Theravance, Inc.

  公开号：EP1685118A2

  公开（公告）日：2006-08-02