2-formylphenyl 3-nitrobenzenesulfonate | 952424-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-formylphenyl 3-nitrobenzenesulfonate
• 英文别名: 2-Formylphenyl 3-nitrobenzenesulfonate；(2-Formylphenyl) 3-nitrobenzenesulfonate；(2-formylphenyl) 3-nitrobenzenesulfonate
• CAS: 952424-60-1
• 化学式: C₁₃H₉NO₆S
• 分子量: 307.284
• InChiKey: SUWXIYSMWDYBBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  513.2±50.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103.58
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-formylphenyl 3-nitrobenzenesulfonate 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 [2-[[(5R,5aS,8aR,9R)-5a-chloro-6-oxo-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]oxymethyl]phenyl] 3-nitrobenzenesulfonate
  参考文献：
  名称：

  Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo

  摘要：

  In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 14 novel 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 9c' and 9g' exhibited the most promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. Generally, it was preliminarily demonstrated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxins might be important for the insecticidal activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.075
• 作为产物：
  描述：

  水杨醛 、 3-硝基苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以57%的产率得到2-formylphenyl 3-nitrobenzenesulfonate
  参考文献：
  名称：

  Design and Synthesis of Novel N-Benzylidenesulfonohydrazide Inhibitors of MurC and MurD as Potential Antibacterial Agents

  摘要：

  一系列新型N-苄叉磺酰肼化合物被设计并合成为大肠杆菌中UDP-N-乙酰胞壁酸:L-丙氨酸连接酶（MurC）和UDP-N-乙酰胞壁酰-L-丙氨酸:D-谷氨酸连接酶（MurD）的抑制剂，这两种酶参与细菌细胞壁的生物合成。部分化合物对这两种酶均显示出抑制活性，其IC50值低至30 μM。此外，还报道了一种新的亚胺基苯甲醛的一锅合成方法。

  DOI：

  10.3390/molecules13010011

文献信息

• New arylsulfonohydrazide inhibitors of enzymes MurC and MurD
  申请人：UNIVERZA V LJUBLJANI, FAKULTETA ZA FARMACIJO

  公开号：EP1845083A3

  公开（公告）日：2009-12-30

  This invention belongs to the field of pharmaceutical chemistry and relates to new arylsulfonohydrazides as inhibitors of UDP-N-acetylmuramyl:L-alanine ligaze (MurC) and UDP-N-acetylmuramyl-L-alanine:D-glutamate ligaze (MurD), to procedures for their preparation and pharmaceutical preparations containing the same. The enzymes MurC and MurD are the key enzymes involved in the synthesis of bacterial peptidoglycan, so arylsulfonohydrazide inhibitors possess antibacterial activity. Compounds of general formula I and the pharmaceutically acceptable salts are described. The appropriate substituents are clearly presented in the body of the text and in claims.

  这项发明属于药物化学领域，涉及新的芳基磺酰肼作为UDP-N-乙酰基葡萄糖胺基莫拉酰基:L-丙氨酸连接酶（MurC）和UDP-N-乙酰基葡萄糖胺基-L-丙氨酸:D-谷氨酸连接酶（MurD）的抑制剂，以及它们的制备方法和含有相同物质的药物制剂。酶MurC和MurD是参与细菌肽聚糖合成的关键酶，因此芳基磺酰肼抑制剂具有抗菌活性。描述了一般式I的化合物及其药用盐。适当的取代基在文本主体和权利要求中清晰呈现。
• Design and Synthesis of Novel N-Benzylidenesulfonohydrazide Inhibitors of MurC and MurD as Potential Antibacterial Agents
  作者：Rok Frlan、Andreja Kovač、Didier Blanot、Stanislav Gobec、Slavko Pečar、Aleš Obreza

  DOI：10.3390/molecules13010011

  日期：——

  A series of novel N-benzylidenesulfonohydrazide compounds were designedand synthesized as inhibitors of UDP-N-acetylmuramic acid:L-alanine ligase (MurC) andUDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase (MurD) from E. coli, involved inthe biosynthesis of bacterial cell-walls. Some compounds possessed inhibitory activityagainst both enzymes with IC50 values as low as 30 μM. In addition, a new, one-potsynthesis of amidobenzaldehydes is reported.

  一系列新型N-苄叉磺酰肼化合物被设计并合成为大肠杆菌中UDP-N-乙酰胞壁酸:L-丙氨酸连接酶（MurC）和UDP-N-乙酰胞壁酰-L-丙氨酸:D-谷氨酸连接酶（MurD）的抑制剂，这两种酶参与细菌细胞壁的生物合成。部分化合物对这两种酶均显示出抑制活性，其IC50值低至30 μM。此外，还报道了一种新的亚胺基苯甲醛的一锅合成方法。
• Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo
  作者：Hui Xu、Jun-Liang Zhang

  DOI：10.1016/j.bmcl.2011.07.075

  日期：2011.9

  In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 14 novel 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 9c' and 9g' exhibited the most promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. Generally, it was preliminarily demonstrated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxins might be important for the insecticidal activity. (C) 2011 Elsevier Ltd. All rights reserved.