3-nitroso-2-phenylbenzo[d]imidazo[2,1-b]thiazole | 17833-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-nitroso-2-phenylbenzo[d]imidazo[2,1-b]thiazole
• 英文别名: 1-Nitroso-2-phenylimidazo[2,1-b][1,3]benzothiazole
• CAS: 17833-13-5
• 化学式: C₁₅H₉N₃OS
• 分子量: 279.322
• InChiKey: CQOZPFVGPDOVRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-nitroso-2-phenylbenzo[d]imidazo[2,1-b]thiazole 在 盐酸 、 对甲苯磺酸 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 4-phenyl-4-(propan-2-yloxy)-4H-[1,2,4]oxadiazolo[3,4-c][1,4]-benzothiazin-1-one
  参考文献：
  名称：

  Understanding Oxadiazolothiazinone Biological Properties: Negative Inotropic Activity versus Cytochrome P450-Mediated Metabolism

  摘要：

  We present a series of oxadiazolothiazinones, selective inotropic agents on isolated cardiac tissues, devoid of chronotropy and vasorelaxant activity. Functional and binding data for the precursor of the series (compound 1) let us hypothesize LTCC blocking activity and the existence of a recognition site specific for this scaffold. We synthesized and tested 22 new derivatives: introducing a para-methoxyphenyl at C-8 led to compound 12 (EC50 = 0.022 mu M), twice as potent as its para-bromo analogue (1). For 10 analogues, we extended the characterization of the biological properties by including the assessment of metabolic stability in human liver microsomes and cytochrome P450 inhibition potential. We observed that the methoxy group led to active compounds with low metabolic stability and high CYP inhibition, whereas the protective effect of bromine resulted in enhanced metabolic stability and reduced CYP inhibition. Thus, we identified two para-bromo benzothiazino-analogues as candidates for further studies.

  DOI：

  10.1021/acs.jmedchem.6b00030
• 作为产物：
  描述：

  2-phenylimidazo[2,1-b]benzothiazole 在 亚硝酸特丁酯 作用下， 以 二氯甲烷 为溶剂， 以83 %的产率得到3-nitroso-2-phenylbenzo[d]imidazo[2,1-b]thiazole
  参考文献：
  名称：

  连续流动和无外部光催化剂、氧化剂和添加剂条件下咪唑并[1,2-a]吡啶的光催化 C3–H 亚硝基化

  摘要：

  本研究报告了一种在可见光照射和连续流相结合的情况下，在没有任何外部光催化剂的情况下，在 C3 位置对咪唑并[1,2- a ]吡啶支架进行高度区域选择性光催化 C-H 亚硝基化的方案。该方案涉及温和、安全的条件，对空气和水表现出良好的耐受性，以及出色的官能团相容性和位点选择性，在光催化剂、氧化剂和添加剂的作用下以优异的产率生成各种3-亚硝基咪唑并[1,2- a ]吡啶值得注意的是，由于亚硝基化的强光吸收特性，所提出的亚硝基化反应将发色团NO引入咪唑并[1,2- a ]吡啶支架中，在可见光照射下有效发生，无需任何额外的光催化剂产品。这项研究可以指导未来开发具有广泛潜在应用的绿色有机合成策略的研究。

  DOI：

  10.1021/acs.joc.4c00173

文献信息

• Regioselective synthesis of nitrosoimidazoheterocycles using tert-butyl nitrite
  作者：Kamarul Monir、Monoranjan Ghosh、Sourav Jana、Pallab Mondal、Adinath Majee、Alakananda Hajra

  DOI：10.1039/c5ob01345c

  日期：——

  A simple and practical method has been developed for the regioselective nitrosylation of imidazopyridines via C(sp²)–H bond functionalization using tert-butyl nitrite under mild reaction conditions.

  一种简单实用的方法已经被开发出来，用于在温和的反应条件下通过C(sp²)–H键功能化使用叔丁基硝酸酯对咪唑吡啶进行区域选择性的亚硝化。
• 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
  申请人：DOOSAN CORPORATION 주식회사 두산(119987140410) Corp. No ▼ 110111-0013774BRN ▼107-81-00237

  公开号：KR101599585B1

  公开（公告）日：2016-03-03

  본 발명은 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 축합이미다조인돌계 화합물이 유기 전계 발광 소자용 재료, 바람직하게는 발광층의 호스트 재료로 도입됨으로써, 유기 전계 발광 소자의 발광효율, 구동 전압 및 수명 등의 전반적인 특성을 향상시킨 것이다.

  本发明涉及新的有机化合物以及包含该化合物的有机电致发光器件，其中含有聚咪唑啉类化合物作为有机电致发光器件的材料，最好是作为发光层的宿主材料引入，从而提高了有机电致发光器件的发光效率、驱动电压和寿命等整体特性。
• Pentimalli,L. et al., Gazzetta Chimica Italiana, 1967, vol. 97, p. 1286 - 1293
  作者：Pentimalli,L. et al.

  DOI：——

  日期：——
• US4497817A
  申请人：——

  公开号：US4497817A

  公开（公告）日：1985-02-05
• Understanding Oxadiazolothiazinone Biological Properties: Negative Inotropic Activity versus Cytochrome P450-Mediated Metabolism
  作者：Emanuele Carosati、Barbara Cosimelli、Pierfranco Ioan、Elda Severi、Kasiram Katneni、Francis C. K. Chiu、Simona Saponara、Fabio Fusi、Maria Frosini、Rosanna Matucci、Matteo Micucci、Alberto Chiarini、Domenico Spinelli、Roberta Budriesi

  DOI：10.1021/acs.jmedchem.6b00030

  日期：2016.4.14

  We present a series of oxadiazolothiazinones, selective inotropic agents on isolated cardiac tissues, devoid of chronotropy and vasorelaxant activity. Functional and binding data for the precursor of the series (compound 1) let us hypothesize LTCC blocking activity and the existence of a recognition site specific for this scaffold. We synthesized and tested 22 new derivatives: introducing a para-methoxyphenyl at C-8 led to compound 12 (EC50 = 0.022 mu M), twice as potent as its para-bromo analogue (1). For 10 analogues, we extended the characterization of the biological properties by including the assessment of metabolic stability in human liver microsomes and cytochrome P450 inhibition potential. We observed that the methoxy group led to active compounds with low metabolic stability and high CYP inhibition, whereas the protective effect of bromine resulted in enhanced metabolic stability and reduced CYP inhibition. Thus, we identified two para-bromo benzothiazino-analogues as candidates for further studies.