3-氨基-3-苯并[1,3]二恶酚-5-基-丙酸乙酯盐酸盐 | 149498-94-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-氨基-3-苯并[1,3]二恶酚-5-基-丙酸乙酯盐酸盐
• 英文名称: ethyl 3-amino-3-(1,3-benzodioxol-5-yl)-propanoate hydrochloride
• 英文别名: ethyl (+/-)-3-amino-3-benzo[1,3]dioxol-5-ylpropanoate hydrochloride；3-amino-3-benzo[1,3]dioxol-5-yl-propionic acid ethyl ester; hydrochloride；3-Amino-3-benzo[1,3]dioxol-5-yl-propionsaeure-aethylester; Hydrochlorid；ethyl 3-amino-3-(1,3-benzodioxol-5-yl)propanoate hydrochloride；ethyl 3-amino-3-(1,3-benzodioxol-5-yl)propionate hydrochloride；Ethyl β-amino-1,3-benzodioxole-5-propanoate.HCl；3-Amino-3-benzo[1,3]dioxol-5-yl-propionic acidethyl ester hydrochloride；ethyl 3-amino-3-(1,3-benzodioxol-5-yl)propanoate;hydrochloride
• CAS: 149498-94-2
• 化学式: C₁₂H₁₅NO₄*ClH
• 分子量: 273.716
• InChiKey: NKQHQIJWIYNEIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.52
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  70.8
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3-氨基-3-苯并[1,3]二恶酚-5-基-丙酸乙酯盐酸盐 在 lithium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 β-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-1,3-benzodioxole-5-propanoic acid
  参考文献：
  名称：

  Potent in Vitro and in Vivo Inhibitors of Platelet Aggregation Based Upon the Arg-Gly-Asp Sequence of Fibrinogen. (Aminobenzamidino)succinyl (ABAS) Series of Orally Active Fibrinogen Receptor Antagonists

  摘要：

  Our initial orally active fibrinogen receptor antagonist benzamidinopentanoyl (BAP) series which was discovered through truncation of our iv antiplatelet agent (SC-52012) demonstrated modest oral activity in canine studies (ethyl [5-(4-amidinophenyl)pentanoyl]3-3-amino-3 pyridyl)propionate, 1e). Introduction of an amide bond adjacent to the benzamidine led to a novel series with an (aminobenzamidino)succinyl (ABAS) Arg-Gly surrogate that had improved in vitro potency (5-17 times) relative to the BAP series. Four ester prodrug/acid active metabolite pairs (2a/2e, 60a/60e, 62a/62e, 63a/63e) from the ABAS series which varied in their 3-substituent on the beta-amino ester ''aspartate mimetic'' were prepared in enantiomerically enriched form (>95:5), and they were evaluated in canine studies for their ability to block collagen-induced aggregation in platelet-rich plasma, the elimination profile (t(1/2) beta-phase), repeated oral dosing studies, and oral systemic availability. Of the four ester prodrug/acid active metabolite pairs, 2e/2a (SC-54684A/SC-54701A) had the most favorable properties in the above studies with an IC50 = 67 +/- 5 nM (dog platelet-rich plasma, collagen), t(1/2) beta = 1.6 h tester) and 6.5 h (acid), no adverse effects upon repeated dosing, and a drug oral systemic availability of 62% (area under curve (AUG) of acid 2a (drug) following ig administration of ester 2e (prodrug, 2.5 mg/kg) divided by AUC of acid 2a (drug) following iv administration of ester 2e (prodrug, 2.5 mg/kg) as determined by HPLRC). In further pharmacokinetic studies using nonlabeled 2e/2a, the oral systemic availability tester 2e ig/ester 2e iv) of 2e was measured to be in the range of 44.7-53.0%. The more biologically relevant oral systemic availability tester 2e ig/acid 2a iv) of 2e was found to be in the range of 22.0-26.4%. A pharmacophore model. based on inhibitors from several different benzamidine classes including 2a (ABAS class) was developed using a combination of molecular modeling (MM2) and pharmacophore identification (APOLLO) methods.

  DOI：

  10.1021/jm00013a014
• 作为产物：
  描述：

  胡椒醛 在 乙酸铵 、 丙二酸 作用下， 以 盐酸 、 乙醇 为溶剂， 生成 3-氨基-3-苯并[1,3]二恶酚-5-基-丙酸乙酯盐酸盐
  参考文献：
  名称：

  Substituted heterocyclic derivatives useful as platelet aggregation

  摘要：

  提供了一种替代的新型杂环衍生物，可以抑制血小板聚集。该发明还涉及制药组合物和使用这些衍生物的方法。

  公开号：

  US05254573A1

文献信息

• Nitrogen heterocycle biaryls for osteoporosis and other diseases
  申请人：Letourneau John Jeffrey

  公开号：US20050222203A1

  公开（公告）日：2005-10-06

  Nitrogen heterocycle biaryls having a carboxylate terminus are useful for treating endometriosis, osteoporosis, restenosis following angioplasty, rheumatoid arthritis, cancer, macular degeneration and obesity. Compounds of formula: are disclosed. A representative example is

  氮杂环联苯具有羧酸末端，可用于治疗子宫内膜异位症、骨质疏松症、血管成形术后再狭窄、类风湿关节炎、癌症、黄斑变性和肥胖症。 公开了以下化合物的结构： 代表性示例是
• Substituted heterocyclic derivatives useful as platelet aggregation
  申请人：Monsanto Company

  公开号：US05254573A1

  公开（公告）日：1993-10-19

  Novel substituted heterocyclic derivatives are provided which inhibit platelet aggregation. This invention also pertains to pharmaceutical compositions and methods of using such derivatives.

  提供了一种替代的新型杂环衍生物，可以抑制血小板聚集。该发明还涉及制药组合物和使用这些衍生物的方法。
• An efficient new enzymatic method for the preparation of β-aryl-β-amino acid enantiomers
  作者：Gábor Tasnádi、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2008.08.009

  日期：2008.9

  An efficient synthesis of β-aryl-β-amino acid enantiomers has been developed via the lipase-catalysed enantioselective hydrolysis of the corresponding racemic ethyl esters in an organic solvent. High enantioselectivities (E >100) were observed when the lipase PS-catalysed reactions were performed with H2O (0.5 equiv) in diisopropyl ether at 45 °C. The products could be easily separated and were obtained

  通过在有机溶剂中通过脂肪酶催化的相应外消旋乙酯的对映选择性水解，已经开发了β-芳基-β-氨基酸对映体的有效合成。当脂肪酶PS催化的H 2 O（0.5当量）在二异丙醚中于45°C进行时，观察到高对映选择性（E > 100）。产物易于分离，收率⩾40％。
• Piperazinone derivatives and their uses
  申请人：Laboratoire L. Lafon

  公开号：US06344456B1

  公开（公告）日：2002-02-05

  The invention concerns compounds of formula (I) wherein R1, R2, R3, R4 and R5 are as defined herein. Said compounds are useful in therapy as antithrombotic agents.

  该发明涉及公式（I）中的化合物，其中R1、R2、R3、R4和R5如本文所定义。所述化合物在治疗中作为抗血栓药物是有用的。
• Tricyclic compounds, preparation method and said method intermediates, application as medicines and pharmaceutical compositions containing same
  申请人：Aventis Pharma S.A.

  公开号：US06339082B1

  公开（公告）日：2002-01-15

  A compound selected from the group consisting of a compound of the formula wherein the substituents are defined as set forth in the specification and its salts with non-toxic pharmaceutically acceptable acids and bases useful for treating loss of bone matrix.

  从以下公式中选择的化合物，其中取代基如规范中所述，并且其盐与非毒性药用可接受酸和碱有用于治疗骨基质丢失的化合物。