N-(5-硝基苯并[d]恶唑-2-基)苯甲酰胺 | 100817-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: N-(5-硝基苯并[d]恶唑-2-基)苯甲酰胺
• 英文名称: N-(5-nitrobenzo[d]oxazol-2-yl)benzamide
• 英文别名: N-(5-nitro-1,3-benzoxazol-2-yl)benzamide
• CAS: 100817-84-3
• 化学式: C₁₄H₉N₃O₄
• 分子量: 283.243
• InChiKey: WLXIAGOSVHUEBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-benzoyl-(3-nitrophenyl)thiourea 在 碘苯二乙酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以221 mg的产率得到N-(5-硝基苯并[d]恶唑-2-基)苯甲酰胺
  参考文献：
  名称：

  二乙酰氧基碘苯通过顺序酰化和脱酰过程辅助C–O键形成：苯并恶唑酰胺的合成及其DFT机理的研究†

  摘要：

  在这项工作中描述了一种使用二乙酰氧基碘苯（DIB）将N-取代的-N'-苯甲酰基硫脲转化为取代的N-苯并恶唑-2-基-酰胺的有效方法。由于DIB的氧化脱氢作用，该转变遵循的是C–O键的形成导致苯并恶唑衍生物的产生，而不是苯并噻唑部分的预期的C–S键的形成。导致苯并恶唑的C–O键形成是由于连续的酰化和脱酰作用以及两摩尔DIB的减少。提出了合理的反应机理，并进行了密度泛函计算以研究反应机理。

  DOI：

  10.1039/c6ob00968a

文献信息

• Synthesis of Benzoxazole Amides as Novel Antifungal Agents against Malassezia Furfur
  作者：Beom-Joon Kim、Jin-Ah Kim、Young-Kook Kim、Soon-Yong Choi、Hea-Young ParkChoo

  DOI：10.5012/bkcs.2010.31.5.1270

  日期：2010.5.20

  Malassezia is a pathogenic fungus that causes skin diseases, such as tinea versicolor, atopic dermatitis and fatal sepsis. We report the synthesis of a series of benzoxazole amides and evaluation of their antifungal activity against Malassezia furfur. Twelve benzoxazole amides were prepared through the cyclization of the substituted 2-hydroxy aniline with N-(bis-methylsulfanylmethylene) amides. Among the prepared compounds, the compounds 4a, 8b, 8c and 8d showed in vitro antifungal activity.

  马拉色菌是一种致病真菌，可引起皮肤病，如皮肤癣菌、特应性皮炎和致命的败血症。我们报告了一系列苯并恶唑酰胺的合成及其对糠秕马拉色菌抗真菌活性的评估。通过将取代的 2- 羟基苯胺与 N-（双甲硫基亚甲基）酰胺环化，制备了 12 种苯并恶唑酰胺类化合物。在制备的化合物中，化合物 4a、8b、8c 和 8d 具有体外抗真菌活性。
• USE OF BENZO-HETEROCYCLE DERIVATIVES FOR PREVENTING AND TREATING CANCER OR FOR INHIBITING CANCER METASTASIS
  申请人：SNU R&DB Foundation

  公开号：EP2497471A2

  公开（公告）日：2012-09-12

  This application relates to a novel benzo-heterocycle derivative and more particularly, it relates a composition for preventing and treating cancer or for inhibiting metastasis comprising benzo-heterocycle derivative or pharmaceutically acceptable salts thereof as an active ingredient. The present inventors confirmed that KRS has an effect on cancer metastasis by facilitating cancer (or tumor) cell migration through interaction with 67LR, and also found that a substance inhibiting the interaction between KRS and 67LR can prevent and treat cancer by inhibiting cancer cell metastasis. Accordingly, the composition of the present invention can inhibit cancer metastasis, and thus provide a novel means for prevention and treatment of cancer.

  本申请涉及一种新型苯并异环衍生物，更具体地说，它涉及一种用于预防和治疗癌症或抑制转移的组合物，其活性成分包括苯并异环衍生物或其药学上可接受的盐。本发明者证实，KRS 通过与 67LR 相互作用促进癌（或肿瘤）细胞迁移，从而对癌症转移产生影响，还发现抑制 KRS 与 67LR 相互作用的物质可以通过抑制癌细胞转移来预防和治疗癌症。因此，本发明的组合物可以抑制癌症转移，从而为癌症的预防和治疗提供了一种新的手段。
• Use of benzo-heterocycle derivatives for preventing and treating cancer or for inhibiting cancer metastasis
  申请人：Kim Sunghoon

  公开号：US10130611B2

  公开（公告）日：2018-11-20

  This application relates to a novel benzo-heterocycle derivative and more particularly, it relates a composition for preventing and treating cancer or for inhibiting metastasis comprising benzo-heterocycle derivative or pharmaceutically acceptable salts thereof as an active ingredient. The present inventors confirmed that KRS has an effect on cancer metastasis by facilitating cancer (or tumor) cell migration through interaction with 67LR, and also found that a substance inhibiting the interaction between KRS and 67LR can prevent and treat cancer by inhibiting cancer cell metastasis. Accordingly, the composition of the present invention can inhibit cancer metastasis, and thus provide a novel means for prevention and treatment of cancer.

  本申请涉及一种新型苯并异环衍生物，更具体地说，它涉及一种用于预防和治疗癌症或抑制转移的组合物，其活性成分包括苯并异环衍生物或其药学上可接受的盐。本发明者证实，KRS 通过与 67LR 相互作用促进癌（或肿瘤）细胞迁移，从而对癌症转移产生影响，还发现抑制 KRS 与 67LR 相互作用的物质可以通过抑制癌细胞转移来预防和治疗癌症。因此，本发明的组合物可以抑制癌症转移，从而为癌症的预防和治疗提供了一种新的手段。
• EP2497471B1
  申请人：——

  公开号：EP2497471B1

  公开（公告）日：2015-04-15
• Diacetoxyiodobenzene assisted C–O bond formation via sequential acylation and deacylation process: synthesis of benzoxazole amides and their mechanistic study by DFT
  作者：Lokendrajit Nahakpam、Francis A. S. Chipem、Brajakishor S. Chingakham、Warjeet S. Laitonjam

  DOI：10.1039/c6ob00968a

  日期：——

  benzoxazole derivative, due to oxidative dehydrogenation by DIB, instead of the expected C–S bond formation of the benzothiazole moiety. The C–O bond formation leading to benzoxazole is due to consecutive acylation and deacylation in conjunction with the reduction of two moles of DIB. A plausible mechanism was proposed for the reaction and density functional calculations were also performed to study the reaction

  在这项工作中描述了一种使用二乙酰氧基碘苯（DIB）将N-取代的-N'-苯甲酰基硫脲转化为取代的N-苯并恶唑-2-基-酰胺的有效方法。由于DIB的氧化脱氢作用，该转变遵循的是C–O键的形成导致苯并恶唑衍生物的产生，而不是苯并噻唑部分的预期的C–S键的形成。导致苯并恶唑的C–O键形成是由于连续的酰化和脱酰作用以及两摩尔DIB的减少。提出了合理的反应机理，并进行了密度泛函计算以研究反应机理。