1-nitro-10H-phenoxazine-3-sulfonylchloride | 1428264-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-nitro-10H-phenoxazine-3-sulfonylchloride
• 英文别名: 1-Nitro-10h-phenoxazine-3-sulfonyl chloride
• CAS: 1428264-06-5
• 化学式: C₁₂H₇ClN₂O₅S
• 分子量: 326.717
• InChiKey: NOGWJYFIDLSPBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-nitro-10H-phenoxazine-3-sulfonylchloride 在 氨 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 15-Phenyl-8-oxa-1,14-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-2,4,6,9,11,13(16),14-heptaene-11-sulfonamide
  参考文献：
  名称：

  Novel imidazophenoxazine-4-sulfonamides: Their synthesis and evaluation as potential inhibitors of PDE4

  摘要：

  A number of novel imidazophenoxazine-4-sulfonamides have been designed as potential inhibitors of PDE4. All these compounds were readily prepared via an elegant multi-step method involving the initial construction of 1-nitro-10H-phenoxazine ring and then fused imidazole ring as key steps. Some of these compounds showed promising PDE4B and D inhibition when tested in vitro and good interactions with these proteins in silico. Three of these compounds showed dose dependent inhibition of PDE4B with IC50 value of 3.31 +/- 0.62, 1.23 +/- 0.18 and 0.53 +/- 0.18 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.023
• 作为产物：
  描述：

  potassium 4-chloro-3,5-dinitrobenzenesulfonate 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1-nitro-10H-phenoxazine-3-sulfonylchloride
  参考文献：
  名称：

  Novel imidazophenoxazine-4-sulfonamides: Their synthesis and evaluation as potential inhibitors of PDE4

  摘要：

  A number of novel imidazophenoxazine-4-sulfonamides have been designed as potential inhibitors of PDE4. All these compounds were readily prepared via an elegant multi-step method involving the initial construction of 1-nitro-10H-phenoxazine ring and then fused imidazole ring as key steps. Some of these compounds showed promising PDE4B and D inhibition when tested in vitro and good interactions with these proteins in silico. Three of these compounds showed dose dependent inhibition of PDE4B with IC50 value of 3.31 +/- 0.62, 1.23 +/- 0.18 and 0.53 +/- 0.18 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.023

文献信息

• Construction of phenoxazine rings containing nitro and sulfonic acid groups leading to phenoxazine-3-sulfonamide derivatives: their evaluation as novel and potential insulin secretagogues
  作者：Seelam Venkata Reddy、Gangula Mohan Rao、Baru Vijaya Kumar、Koppela Naresh Reddy、Konda Sravya、Puchchakayala Goverdhan、Vandana Rathore、Girdhar Singh Deora、Manojit Pal

  DOI：10.1039/c3md00377a

  日期：——

  designed, synthesized and evaluated for its hypoglycemic, hyperglycemic and oral anti-diabetic activities. These compounds were prepared via the construction of a phenoxazine ring containing nitro and sulfonic acid groups in a single step followed by further transformations. One of these compounds exhibited promising anti-diabetic activities comparable to glibenclamide and increased serum insulin levels

  设计，合成和评估了一系列N-（烷基/芳基/杂芳基）-1-硝基-10 H-吩恶嗪-3-磺酰胺，其降血糖，高血糖和口服降糖活性。通过在单个步骤中构建包含硝基和磺酸基团的吩恶嗪环，然后进行进一步的转化来制备这些化合物。这些化合物之一显示出与格列本脲相当的有希望的抗糖尿病活性，并且血清胰岛素水平升高，表明其作为新型胰岛素促分泌剂的潜力。