3-benzyl-2H-benzo[e][1,3]oxazine-2,4(3H)-dione | 2037-99-2

• 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: 3-benzyl-2H-benzo[e][1,3]oxazine-2,4(3H)-dione
• 英文别名: 3-benzyl-2H-1,3-benzoxazine-2,4(3H)-dione；3-benzyl-1,3-benzoxazine-2,4(3H)-dione；3-benzylbenzo[e]-1,3-oxazine-2,4-dione；3-benzylbenzoxazine-2,4-dione；3-benzyl-benzo[e][1,3]oxazine-2,4-dione；3-benzyl-benz[e][1,3]oxazine-2,4-dione；3-Benzyl-benzo[e][1,3]oxazine-2,4-dione；3-benzyl-1,3-benzoxazine-2,4-dione
• CAS: 2037-99-2
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: WDEVZFISTMLQTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyl-2H-benzo[e][1,3]oxazine-2,4(3H)-dione 、 Ammonium hydroxide 生成 N-苄基-2-羟基-苯甲酰胺
  参考文献：
  名称：

  Bogisch, Dissert. , S. 23

  摘要：

  DOI：
• 作为产物：
  描述：

  邻乙酰水杨酰氯 在 盐酸 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.67h， 生成 3-benzyl-2H-benzo[e][1,3]oxazine-2,4(3H)-dione
  参考文献：
  名称：

  Design and synthesis of novel bone-targeting dual-action pro-drugs for the treatment and reversal of osteoporosis

  摘要：

  There is an important medical need for effective therapies to redress the general bone loss associated with advanced osteoporosis. Prostaglandin E-2 and related EP4 receptor agonists have been shown to stimulate bone regrowth but their use has been limited by systemic side effects. Herein is described the design and synthesis of novel dual-action bone-targeting conjugate pro-drugs where two classes of active agents, a bone growth stimulating prostaglandin E-2 EP4 receptor subtype agonist (5 or 6) and a bone resorption inhibitor bisphosphonate, alendronic acid (1), are coupled using metabolically labile carbamate or 4-hydroxyphenylacetic acid based linkers. Radiolabelled conjugates 9, 11a/b and 25 were synthesized and evaluated in vivo in rats for uptake of the conjugate into bone and subsequent release of the EP4 agonists over time. While conjugate 11a/b was taken up (9.0% of initial dose) but not released over two weeks, conjugates 9 and 25 were absorbed at 9.4% and 5.9% uptake of the initial dose and slowly released with half-lives of approximately 2 weeks and 5 days respectively. These conjugates were well tolerated and offer potential for sustained release and dual synergistic activity through their selective bone targeting and local release of the complimentary active components. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.024

文献信息

• <i>N</i>-Alkylation of imides using phase transfer catalysts under solvent-free conditions
  作者：Jolanta Jaśkowska、Piotr Kowalski

  DOI：10.1002/jhet.5570450519

  日期：2008.9

  N-Alkylation of imides in the reaction of imides and alkylhalides, catalyzed by PT catalysts under solvent-free conditions, has been developed. The reaction occurs in the presence of K2CO3, and in many cases it takes place spontaneously. In the N-benzylation reaction, it has been recognized that TBAB (tetrabutylammonium bromide) and TBATFB (tetrabutylammonium tetrafluoroborate) show highest catalytic

  已经开发了在无溶剂条件下由PT催化剂催化的酰亚胺和烷基卤化物的反应中酰亚胺的N-烷基化。该反应在K 2 CO 3的存在下发生，并且在许多情况下是自然发生的。在N-苄基化反应中，已经认识到TBAB（溴化四丁基铵）和TBAFB（四氟硼酸四丁基铵）显示出最高的催化作用。通过各种酰亚胺的N-苄基化和N-乙基化，已证实了无溶剂烷基化的多功能性和合成能力。所开发的方法使得容易获得N-（ω-溴烷基）酰亚胺。
• The synthesis of cyclic and acyclic long‐chain arylpiperazine derivatives of salicylamide as serotonin receptor ligands
  作者：Piotr Kowalski、Jolanta Jaśkowska、Andrzej J. Bojarski、Beata Duszyńska

  DOI：10.1002/jhet.5570450125

  日期：2008.1

  4-diones as well as O- and N-substituted salicylamides with an n-propyl chain were synthesized in order to explore the effect of cyclic and acyclic salicylamide moieties on their binding affinity for 5-HT1A, 5-HT2A and 5-HT7 receptor sites. Target compounds 1 and 2 were prepared by a two-step procedure, i.e. by alkylation of 1,3-benzoxazine-2,4-dione or salicylamide with 1,3-dibromopropane and next by condensation

  合成了N-取代的1,3-苯并恶嗪-2,4-二酮的1-芳基哌嗪系列以及具有正丙基的O-和N-取代的水杨酰胺，以研究环状和无环水杨酰胺部分的作用它们对5-HT 1A，5-HT 2A和5-HT 7受体位点的结合亲和力。目标化合物1和2通过两步程序制备，即通过将1，3-苯并恶嗪-2，4-二酮或水杨酰胺与1，3-二溴丙烷烷基化，然后使3-溴丙基中间体与芳基哌嗪缩合；3-溴丙基中间体的合成在无溶剂条件下进行。通过水解1制备化合物3。关于水杨酰胺部分，对于相同的芳基哌嗪，对5-HT 1A和5-HT 7受体的结合亲和力根据衍生物3＜1＜2的等级而增加。关于5-HT 2A受体，配体活性的增加以与5-HT 1A的亲和力相反的顺序改变，即2 < 1 < 3。5-HT 1A和5-HT 7受体的结合常数对于2-甲氧基苯基配体2c最高，而3-氯苯基配体3b对5-HT 2A受体最活跃。
• A note to the biological activity of benzoxazine derivatives containing the thioxo group
  作者：Karel Waisser、Eva Petrlíková、Milan Peřina、Věra Klimešová、Jiří Kuneš、Karel Palát、Jarmila Kaustová、Hans-Martin Dahse、Ute Möllmann

  DOI：10.1016/j.ejmech.2010.02.037

  日期：2010.7

  synthesized. The compounds were tested for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium. The replacement of the carbonyl group by the thiocarbonyl group increased the antimycobacterial activity. The most active derivatives were more active than isonicotinhydrazide (INH). The cytotoxicity and the antiproliferative activity were studied as

  合成了新的3-苄基-4-thioxo-2 H -1,3-苯并恶嗪-2（3 H）-1和3-苄基-2 H -1,3-苯并恶嗪-2,4（3 H）-二硫。测试了这些化合物对结核分枝杆菌，堪萨斯分枝杆菌和鸟分枝杆菌的体外抗分枝杆菌活性。用硫代羰基取代羰基提高了抗分枝杆菌的活性。活性最高的衍生物比异烟肼（INH）更具活性。还研究了细胞毒性和抗增殖活性。
• A Simple One-Pot Synthesis of Benzoxazine-2,4-diones and Benzothiazine-2,4-diones
  作者：Nigel H. Greig、Xiaoxiang Zhu、Qian-sheng Yu、Judith L. Flippen-Anderson、Arnold Brossi

  DOI：10.3987/com-02-s2

  日期：——
• Crum,J.D.; Franks,J.A., Journal of Heterocyclic Chemistry, 1965, vol. 2, p. 37 - 40
  作者：Crum,J.D.、Franks,J.A.

  DOI：——

  日期：——

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