N-[2-(2,3,8,9-tetrahydro-7H-indeno[4,5-b]-1,4-dioxin-9-yl)ethyl]propionamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: N-[2-(2,3,8,9-tetrahydro-7H-indeno[4,5-b]-1,4-dioxin-9-yl)ethyl]propionamide
• 英文别名: N-[2-(3,7,8,9-tetrahydro-2H-cyclopenta[h][1,4]benzodioxin-9-yl)ethyl]propanamide
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: ISWKMBFZJOJGPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6,7-二甲氧基-1-茚满酮 在 Raney-Co 氨 、 氢气 、 三溴化硼 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 copper(II) oxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， -20.0~140.0 ℃ 、480.01 kPa 条件下， 反应 18.0h， 生成 N-[2-(2,3,8,9-tetrahydro-7H-indeno[4,5-b]-1,4-dioxin-9-yl)ethyl]propionamide
  参考文献：
  名称：

  合成一系列新的三环茚满衍生物作为褪黑激素受体激动剂。

  摘要：

  为了开发一种新的睡眠障碍治疗剂，我们合成了一系列新的三环茚满衍生物，并评估了它们与褪黑激素受体的结合亲和力。在我们以前的论文中，我们提出了甲氧基的构型，有利于MT（1）受体的结合。为了将甲氧基固定在一个活性构象中，我们决定合成构象受限的三环茚满类似物，将其在呋喃，1,3-二恶烷，恶唑，吡喃，吗啉或1,4-中的6-位氧原子合成二恶烷环系统。在这些化合物中，茚并[5,4-b]呋喃类似物被发现是最有效和最具选择性的MT（1）受体配体，并具有出色的代谢稳定性。取代基的优化导致（S）-（-）-22b，它对人MT（1）的亲和力非常强（K（i）= 0.014 nM），但对仓鼠MT（3）（）（K（i）= 2600 nM）或其他神经递质受体无明显亲和力。在实验动物中研究了（S）-（-）-22b的药理作用，发现以0.1 mg / kg的剂量po可以促进自由活动的猫的睡眠，如清醒性的降低和增加所表明的在慢波睡眠

  DOI：

  10.1021/jm0201159

文献信息

• Bicyclic compounds and pharmaceutical composition containing tricyclic compound for treating or preventing sleep disorders
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1199304A1

  公开（公告）日：2002-04-24

  A compound having the following general fomula: wherein R1 is an optionally substituted hydrocarbon, amino or heterocyclic group; R2 is H or an optionally substituted hydrocarbon group; R3 is H or an optionally substituted hydrocarbon or heterocyclic group; X is CHR4, NR4, O or S in which R4 is H or an optionally substituted hydrocarbon group; R5 is H, a halogen atom, C1-6 alkyl group, a C1-6 alkoxy group, a hydroxy group, a nitro group, a cyano group or an amino group wherein the C1-6 alkyl group, the C1-6 alkoxy group and the amino group may be substituted by 1 to 5 substituents, Y is C or N; ring B is an optionally substituted benzene ring; m = 1 to 4 and n = 0 to 2; L represents a leaving group such as a halogen atom, an alkylsulfonyl group, an alkylsulfonlyoxy group and arylsulfonyloxy group; or a salt thereof.

  具有以下一般式的化合物： 其中R1是可选择取代的碳氢化合物、氨基或杂环基团；R2是H或可选择取代的碳氢基团；R3是H或可选择取代的碳氢基团或杂环基团；X是CHR4、NR4、O或S，其中R4是H或可选择取代的碳氢基团；R5是H、卤素原子、C1-6烷基基团、C1-6烷氧基团、羟基、硝基、氰基或氨基，其中C1-6烷基基团、C1-6烷氧基团和氨基可能被1至5个取代基取代，Y是C或N；环B是可选择取代的苯环；m = 1至4，n = 0至2；L代表离去基团，如卤素原子、烷基磺酰基团、烷基磺酰氧基团和芳基磺酰氧基团；或其盐。
• AGENT FOR PREVENTION/TREATMENT OF IRRITABLE BOWEL SYNDROME
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1997488A1

  公开（公告）日：2008-12-03

  The present invention provides a prophylactic or therapeutic agent for irritable bowel syndrome, which comprises a compound represented by formula (I): wherein, R1 represents an optionally substituted hydrocarbon group, etc., R2 represents a hydrogen atom or an optionally substituted hydrocarbon group, R3 represents a hydrogen atom, an optionally substituted hydrocarbon group, etc., X represents CHR4, NR4, CO, O or S (wherein, R4 represents a hydrogen atom, an optionally substituted hydrocarbon group, etc.),Y represents C, CH or N, represents a single bond or double bond, ring A represents an optionally substituted 5- to 7-membered oxygen-containing heterocyclic ring, ring B represents an optionally substituted benzene ring, and m represents an integer of 1 to 4, or a salt thereof.

  本发明提供了一种肠易激综合征的预防或治疗剂，它由式 (I) 所代表的化合物组成： 其中，R1 代表任选取代的烃基等，R2 代表氢原子或任选取代的烃基，R3 代表氢原子、任选取代的烃基等、X 代表 CHR4、NR4、CO、O 或 S（其中，R4 代表氢原子、任选取代的烃基等），Y 代表 C、CH 或 N，代表单键或双键，环 A 代表任选取代的 5 至 7 元含氧杂环，环 B 代表任选取代的苯环，m 代表 1 至 4 的整数，或其盐。
• PROPHYLACTIC OR THERAPEUTIC AGENT FOR ATTENTION DEFICIT/HYPERACTIVITY DISORDER
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2248808A1

  公开（公告）日：2010-11-10

  The present invention provides a novel prophylactic or therapeutic agent for attention deficit/hyperactivity disorder. A prophylactic or therapeutic agent for attention deficit/hyperactivity disorder, containing (S)-N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide as an active ingredient.

  本发明提供了一种新型预防或治疗注意缺陷/多动障碍的药物。 一种用于注意缺陷/多动症的预防或治疗剂，含有(S)-N-[2-(1,6,7,8-四氢-2H-茚并[5,4-b]呋喃-8-基)乙基]丙酰胺作为活性成分。
• Prophylactic or Therapeutic Agent for Irritable Bowel Syndrome
  申请人：Terauchi Jun

  公开号：US20090048325A1

  公开（公告）日：2009-02-19

  The present invention provides a prophylactic or therapeutic agent for irritable bowel syndrome, which comprises a compound represented by formula (I): wherein, R 1 represents an optionally substituted hydrocarbon group, etc., R 2 represents a hydrogen atom or an optionally substituted hydrocarbon group, R 3 represents a hydrogen atom, an optionally substituted hydrocarbon group, etc., X represents CHR 4 , NR 4 , CO, O or S (wherein, R 4 represents a hydrogen atom, an optionally substituted hydrocarbon group, etc.), Y represents C, CH or N, represents a single bond or double bond, ring A represents an optionally substituted 5- to 7-membered oxygen-containing heterocyclic ring, ring B represents an optionally substituted benzene ring, and m represents an integer of 1 to 4, or a salt thereof.
• PROPHYLACTIC OR THERAPEUTIC AGENT FOR IRRITABLE BOWEL SYNDROME
  申请人：Terauchi Jun

  公开号：US20100267821A1

  公开（公告）日：2010-10-21

  The present invention provides a prophylactic or therapeutic agent for irritable bowel syndrome, which comprises a compound represented by formula (I): wherein, R 1 represents an optionally substituted hydrocarbon group, etc., R 2 represents a hydrogen atom or an optionally substituted hydrocarbon group, R 3 represents a hydrogen atom, an optionally substituted hydrocarbon group, etc., X represents CHR 4 , NR 4 , CO, O or S (wherein, R 4 represents a hydrogen atom, an optionally substituted hydrocarbon group, etc.), Y represents C, CH or N, represents a single bond or double bond, ring A represents an optionally substituted 5- to 7-membered oxygen-containing heterocyclic ring, ring B represents an optionally substituted benzene ring, and m represents an integer of 1 to 4, or a salt thereof.