ethyl (3'-oxo-3',4'-dihydro-2'H-1',4'-benzoxazin-2'-yl)acetate | 77434-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: ethyl (3'-oxo-3',4'-dihydro-2'H-1',4'-benzoxazin-2'-yl)acetate
• 英文别名: ethyl (3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-yl)acetate；ethyl 3,4-dihydro-3-oxo-2H-1,4-benzoxazine-2-acetate；ethyl 3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-acetate；ethyl 2-(3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl]acetate；ethyl 2-(3-oxo-4H-1,4-benzoxazin-2-yl)acetate
• CAS: 77434-73-2
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: FEUXNZSGFSOLDH-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C(Solv: ethanol (64-17-5))
• 沸点：
  400.8±38.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (3'-oxo-3',4'-dihydro-2'H-1',4'-benzoxazin-2'-yl)acetate 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 0.33h， 生成 3,4-二氢-3-氧代-2H-(1,4)-苯并噁嗪-2-基-乙酸
  参考文献：
  名称：

  Yalcin, Ismail; Tekiner, Betul P.; Oren, Ilkay Yildiz, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 4, p. 905 - 909

  摘要：

  DOI：
• 作为产物：
  描述：

  富马酸单乙酯 在 氯化亚砜 、 碳酸氢钠 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 苯 为溶剂， 反应 30.0h， 生成 ethyl (3'-oxo-3',4'-dihydro-2'H-1',4'-benzoxazin-2'-yl)acetate
  参考文献：
  名称：

  Synthesis, antimicrobial activity and QSARs of new benzoxazine-3-ones

  摘要：

  New ethyl 3,4-dihydro-3-oxo-4,6,7-trisubstituted-2H-1,4-benzoxazine-2-acetate derivatives were synthesized and their structures were elucidated by IR, H-1 NMR and mass spectral data. Antimicrobial activity of the compounds was investigated by using the method of twofold serial dilution technique against different Gram-positive, Gram-negative bacteria and some Candida species in comparison to standard drugs. Microbiological results indicated that the synthesized compounds possessed a broad spectrum of activity having MIC values of 6.25-100 mu g/ml against the tested microorganisms. The QSAR analysis of a set of these compounds tested for growth inhibitory activity against Candida krusei was performed by using the computer-assisted multiple regression procedure. The activity contributions for substituent effects of these compounds were determined from the correlation equation for predictions of the lead optimization. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.06.011

文献信息

• Syntheses of 3,4-dihydro-2H-1,4-benzoxazine-2-acetates and related compounds.
  作者：YUTAKA MASUOKA、TSUNEHIKO(deceased) ASAKO、GIICHI GOTO、SHUNSAKU NOGUCHI

  DOI：10.1248/cpb.34.130

  日期：——

  The intramolecular Michael addition of 4-(2-hydroxyanilino)-2-butenoates (3), -2-buteno-nitrile, and their 3-phenyl analogs (8) gave 3, 4-dihydro-2H-1, 4-benzoxazine-2-acetates (4), -2-acetonitrile (6), and their 3-phenyl analogs (9), respectively, in good yields. In addition, 3, 4-dihydro-3-oxo-2H-1, 4-benzoxazine-2-acetates (13) and 3, 4-dihydro-2-(p-nitrobenzyl)-2H-1, 4-benzoxazine (16) were synthesized from 2-hydroxyanilines (1) by the addition reaction of fumaric acid chloride monoester (11) and p-nitrocinnamyl bromide (14), respectively. In order to examine the biological activities of the 2H-1, 4-benzoxazine analogs, 2-(2-dialkylaminoethyl)-(18) and 2-(2, 2-diphenylethyl)-2H-1, 4-benzoxazines (19, 20) were prepared.Among the compounds synthesized, 4b and 19a showed considerable anxiolytic activity in the conflict test in rats, while the oxalates of 18a-c showed potent anticonvulsant activity.

  4-(2-羟基苯氨基)-2-丁烯酸酯(3)、-2-丁烯腈及其3-苯基类似物(8)的分子内Michael加成反应，分别以良好的产率得到了3,4-二氢-2H-1,4-苯并噁嗪-2-乙酸酯(4)、-2-乙腈(6)及其3-苯基类似物(9)。此外，3,4-二氢-3-氧代-2H-1,4-苯并噁嗪-2-乙酸酯(13)和3,4-二氢-2-(对硝基苄基)-2H-1,4-苯并噁嗪(16)分别通过富马酸氯甲酸单酯(11)和对硝基肉桂基溴(14)的加成反应，从2-羟基苯胺(1)合成得到。为了考察2H-1,4-苯并噁嗪类似物的生物活性，合成了2-(2-二烷基氨基乙基)-(18)和2-(2,2-二苯基乙基)-2H-1,4-苯并噁嗪(19, 20)。在所合成的化合物中，4b和19a在小鼠冲突实验中表现出显著的抗焦虑活性，而18a-c的草酸盐则显示出强效的抗惊厥活性。
• 1,4-benzoxazine-2-acetic acid compound, method for production thereof
  申请人：Senju Pharmaceutical Co., Ltd.

  公开号：US05635505A1

  公开（公告）日：1997-06-03

  A 1,4-benzoxazine-2-acetic acid compound of the formula (I) ##STR1## wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof, a method for production thereof, and a pharmaceutical composition, an aldose reductase inhibitor and an agent for the prevention and/or treatment of the complications of diabetes, which contain the same. The compound (I) of the present invention and pharmaceutically acceptable salts thereof have aldose reductase inhibitory action and are superior in safety. Accordingly, they are useful as an agent for the prevention and/or treatment of the complications of diabetes such as faulty union of corneal injury, cataract, neurosis, retinopathy and nephropathy, in particular, cataract and neurosis.

  本发明涉及一种具有式(I)结构的1,4-苯并噁嗪-2-乙酸化合物##STR1##，其中每个符号的定义如说明书中所述，其药学上可接受的盐，其制备方法，以及含有该化合物的药物组合物、醛糖还原酶抑制剂和用于预防和/或治疗糖尿病并发症的药物。本发明的化合物(I)及其药学上可接受的盐具有醛糖还原酶抑制作用，且安全性优越。因此，它们可作为预防和/或治疗糖尿病并发症的药物，如角膜损伤愈合不良、白内障、神经病变、视网膜病变和肾病，特别是白内障和神经病变。
• 1,4-BENZOXAZINE-2-ACETIC ACID COMPOUND, PROCESS FOR PRODUCING THE SAME, AND USE THEREOF
  申请人：Senju Pharmaceutical Co., Ltd.

  公开号：EP0738727A1

  公开（公告）日：1996-10-23

  A 1,4-benzoxazine-2-acetic acid compound of the formula (I) wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof, a method for production thereof, and a pharmaceutical composition, an aldose reductase inhibitor and an agent for the prevention and/or treatment of the complications of diabetes, which contain the same. The compound (I) of the present invention and pharmaceutically acceptable salts thereof have aldose reductase inhibitory action and are superior in safety. Accordingly, they are useful as an agent for the prevention and/or treatment of the complications of diabetes such as faulty union of corneal injury, cataract, neurosis, retinopathy and nephropathy, in particular, cataract and neurosis.

  一种式（I）的 1，4-苯并恶嗪-2-乙酸化合物 其中各符号如说明书中所定义、其药学上可接受的盐、其生产方法，以及含有这些成分的药物组合物、醛糖还原酶抑制剂和预防和/或治疗糖尿病并发症的制剂。本发明的化合物(I)及其药学上可接受的盐类具有醛糖还原酶抑制作用，且安全性优越。因此，它们可作为预防和/或治疗糖尿病并发症的药物，如角膜损伤的错合、白内障、神经衰弱、视网膜病变和肾病，特别是白内障和神经衰弱。
• Teitei, Tsutomu, Australian Journal of Chemistry, 1986, vol. 39, # 3, p. 503 - 510
  作者：Teitei, Tsutomu

  DOI：——

  日期：——
• US5635505A
  申请人：——

  公开号：US5635505A

  公开（公告）日：1997-06-03