6-amino-1,2,3,4-tetrahydro-1-oxonaphthalene-2-acetic acid ethyl ester | 164148-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-amino-1,2,3,4-tetrahydro-1-oxonaphthalene-2-acetic acid ethyl ester
• 英文别名: dl-6-amino-1-oxo-1,2,3,4-tetrahydro-naphth-2-yl-acetic acid ethyl ester；ethyl 2-(6-amino-1-oxo-3,4-dihydro-2H-naphthalen-2-yl)acetate
• CAS: 164148-75-8
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: KDLAYVQAMBLXNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-1,2,3,4-tetrahydro-1-oxonaphthalene-2-acetic acid ethyl ester 在 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 生成 {1-Oxo-6-[2-(piperidin-4-yloxy)-acetylamino]-1,2,3,4-tetrahydro-naphthalen-2-yl}-acetic acid
  参考文献：
  名称：

  Fused bicyclic Gly-Asp β-turn mimics with potent affinity for GPIIb-IIIa. Exploration of the arginine isostere

  摘要：

  6-[4-Amidinobenzoyl]amino]-tetralone acid is a potent antagonist of GPIIb-IIIa. substitution in the meta position of the benzamidine, or replacement with a heteroaryl amidine was tolerated in this series. Use of an acyl-linked 4-alkyl piperidine as an arginine isostere also provided active compounds. Compounds from this series provided substantial systemic exposure in the rat following oral administration. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00008-1
• 作为产物：
  描述：

  6-(acetylamino)-1,2,3,4-tetrahydro-1-oxonaphthalene-2-acetic acid 在 盐酸 作用下， 反应 2.5h， 生成 6-amino-1,2,3,4-tetrahydro-1-oxonaphthalene-2-acetic acid ethyl ester
  参考文献：
  名称：

  Fused Bicyclic Gly-Asp β-Turn Mimics with Specific Affinity for GPIIb-IIIa

  摘要：

  Disubstituted isoquinolones 2 and 3 have affinity for GPIIb-IIIa and represent leads for further structural evaluation. Structure-activity studies centered on the bicyclic beta-turn mimic contained in these molecules indicated that this moiety could accommodate a variety of modifications. Specifically, monocyclic, 6,5-bicyclic, and 6,7-bicyclic structures provide compounds with affinity for GPIIb-IIIa. Within the 6,6-series, isoquinoline, tetralin, tetralone, and benzopyran nuclei yield potent antagonists that are specific for GPIIb-IIIa. Attachment of the arginine isostere (benzamidine) to the supporting nucleus can be accomplished with an ether or amide linkage, although the latter enhances activity. Several compounds in this series provided measurable blood levels after oral dosing. Conversion of the acid moiety in these molecules to an ester generally provided compounds which gave greater systemic exposure after oral administration. Absolute bioavailabilities in the rat for the ethyl ester prodrug derivatives of the tetralin, tetralone, and benzopyran analogues of 3 were 28%, 23%, and 24%, respectively.

  DOI：

  10.1021/jm990365y

文献信息

• Tricyclic dihydropyridazinones and pharmaceutical compositions
  申请人：Boehringer Biochemia Robin, S.p.A.

  公开号：US04692447A1

  公开（公告）日：1987-09-08

  The tricyclic dihydropyridazinone derivatives having formula I ##STR1## are endowed with interesting hypotensive, vasodilating, antiaggregant, antithrombotic and cytoprotective properties and are therefore useful in human or veterinary medicine.

  具有以下化学式的三环二氢吡啶并嗪衍生物具有降压、扩血管、抗血小板聚集、抗血栓和细胞保护等有趣的性质，因此在人类或兽医学中具有用途。
• US4692447A
  申请人：——

  公开号：US4692447A

  公开（公告）日：1987-09-08