N-(2-iodo-4-nitrophenyl)methanesulfonamide | 1169434-04-1

• 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: N-(2-iodo-4-nitrophenyl)methanesulfonamide
• CAS: 1169434-04-1
• 化学式: C₇H₇IN₂O₄S
• 分子量: 342.114
• InChiKey: BXRLNVJONDVTMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-iodo-4-nitrophenyl)methanesulfonamide 、 3-(2-(prop-2-ynyloxy)ethyl)-2H-benzo[e][1,3]oxazin-4(3H)-one 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以61%的产率得到3-(2-((1-(methylsulfonyl)-5-nitro-1H-indol-2-yl)methoxy)ethyl)-2H-benzo[e][1,3]oxazin-4(3H)-one
  参考文献：
  名称：

  Synthesis of 2H- 1,3-benzoxazin-4(3 H )-one derivatives containing indole moiety: Their in vitro evaluation against PDE4B

  摘要：

  A number of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole or benzofuran moieties were synthesized by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The o-iodoanilides or o-iodophenol were coupled with 3-{2-(prop-2-ynyloxy) ethyl}-2H-benzo[e][1,3] oxazin-4(3H)-one using 10% Pd/C-CuI-PPh3 as a catalyst system and Et3N as a base to give the target compounds. All the synthesized compounds were tested for their PDE4B inhibitory potential in vitro using a cell based cAMP reporter assay. Some of them showed fold increase of the cAMP level when tested at 30 lM. A representative compound showed encouraging PDE4B inhibitory properties that were supported by its docking results. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.117
• 作为产物：
  描述：

  甲磺酰胺,N-(2-碘苯基)- 在 [双(三氟乙酰氧基)碘]苯 、 sodium nitrite 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以42%的产率得到N-(2-iodo-4-nitrophenyl)methanesulfonamide
  参考文献：
  名称：

  Mild hypervalent iodine mediated oxidative nitration of N-aryl sulfonamides

  摘要：

  已开发出一种无氧化剂和酸的N-芳基磺酰胺硝化方法，该方法采用廉价的亚硝酸钠作为易处理的NO2来源，以及高价碘试剂PIFA作为定量氧化剂。在非常温和的反应条件下，所期望的单硝基芳基磺酰胺以高达87%的产率被分离出来。这是首次报道碘烷介导的氧化硝化反应。

  DOI：

  10.1039/c4cc04738a

文献信息

• AlCl3 mediated unexpected migration of sulfonyl groups: regioselective synthesis of 7-sulfonyl indoles of potential pharmacological interest
  作者：Bagineni Prasad、Raju Adepu、Sandhya Sandra、D. Rambabu、G. Rama Krishna、C. Malla Reddy、Girdhar Singh Deora、Parimal Misra、Manojit Pal

  DOI：10.1039/c2cc35757g

  日期：——

  A conceptually new and straightforward introduction of sulfonyl groups at the C-7 position of an indole ring has been achieved via AlCl3 mediated unexpected regioselective sulfonyl group migration for N-alkyl/aryl/heteroarylsulfonyl indoles affording potential inhibitors of Mycobacterium tuberculosis H37Rv chorismate mutase.

  通过AlCl3介导的N-烷基/芳基/杂芳基磺酰基吲哚意外的区域选择性磺酰基迁移，实现了在吲哚环C-7位引入磺酰基的概念性新方法，这一方法为结核杆菌H37Rv分支酸变位酶的潜在抑制剂提供了可能。
• Novel N-indolylmethyl substituted olanzapine derivatives: their design, synthesis and evaluation as PDE4B inhibitors
  作者：Dhilli Rao Gorja、Soumita Mukherjee、Chandana Lakshmi T. Meda、Girdhar Singh Deora、K. Lalith Kumar、Ankit Jain、Girish H. Chaudhari、Keerthana S. Chennubhotla、Rakesh K. Banote、Pushkar Kulkarni、Kishore V. L. Parsa、K. Mukkanti、Manojit Pal

  DOI：10.1039/c3ob27424a

  日期：——

  A new strategy for converting antipsychotic drug olanzapine into PDE4 inhibitors is described via the design and Pd/C mediated synthesis of novel N-indolylmethyl olanzapine derivatives. One compound showed good inhibition (IC50 1.1 μM) and >10 fold selectivity towards PDE4B over D that was supported by docking studies. This compound also showed significant inhibition of TNF-α and no major toxicities in cell lines and a zebrafish embryo model except the teratogenic effects to be re-assessed in rodents.

  描述了一种将抗精神病药物奥氮平转化为PDE4抑制剂的新策略，通过设计和Pd/C介导合成新型N-吲哚基甲基奥氮平衍生物。一种化合物表现出良好的抑制作用（IC50 1.1 μM），并且对PDE4B的选择性超过PDE4D超过10倍，这得到了对接研究的支持。该化合物还显示出显著抑制TNF-α，并且在细胞系和斑马鱼胚胎模型中没有明显的毒性，除了在啮齿动物中需要重新评估的致畸效应。
• Synthesis of 3-indolylmethyl substituted (pyrazolo/benzo)triazinone derivatives under Pd/Cu-catalysis: Identification of potent inhibitors of chorismate mutase (CM)
  作者：Gangireddy Sujeevan Reddy、Ampalam Venkata Snehalatha、Rebecca Kristina Edwin、Kazi Amirul Hossain、Varadaraj Bhat Giliyaru、Raghu Chandrashekhar Hariharapura、G. Gautham Shenoy、Parimal Misra、Manojit Pal

  DOI：10.1016/j.bioorg.2019.103155

  日期：2019.10

  identification of potential antitubercular agents due to its absence in animals but not in bacteria. A series of 3-indolylmethyl substituted pyrazolotriazinone derivatives were designed and docked into CM in silico as potential inhibitors. These compounds were efficiently synthesized using the Pd/Cu-catalyzed coupling-cyclization in a single pot involving the construction of indole ring. The methodology

  由于在动物中而不存在细菌，所以分支酸突变酶（CM）被认为是用于鉴定潜在抗结核剂的有吸引力的靶标。设计了一系列3-吲哚基甲基取代的吡唑并三嗪酮衍生物，并将其作为潜在的抑制剂对接入计算机硅CM中。这些化合物使用Pd / Cu催化的偶合环化反应在一个涉及吲哚环构建的单一反应釜中有效合成。该方法随后扩展到吡唑并三嗪酮的相应苯并类似物的制备，即3-吲哚基甲基取代的苯并三嗪酮衍生物。在体外测试时，这些新型化合物中的几种对CM具有明显的抑制作用在30 µM。SAR（结构-活性-关系）研究表明，苯并三嗪酮部分比吡唑并三嗪酮环更有利。两种最佳的活性化合物的IC 50 约为0.4-0.9 µM（比所用的参考/已知化合物好），在体外直至30 µM都没有毒性。
• (Aza)indole derivative substituted in position 5, pharmaceutical composition comprising it, intermediate compounds and preparation process therefor
  申请人：Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.p.A.

  公开号：EP2078711A1

  公开（公告）日：2009-07-15

  An (aza)indole derivative substituted in position 5, of formula (I): in which X, Y, Z, G1, G2, G3, R1, W, and R2 have the meanings given in the description, a pharmaceutical composition comprising it, and also intermediate compounds and a preparation process therefor.

  一种在位置5被取代的(aza)吲哚衍生物，化学式为(I)：其中X、Y、Z、G1、G2、G3、R1、W和R2的含义如描述中所述，包括它的药物组合物，以及中间化合物和制备方法。
• (AZA)INDOLE DERIVATIVE SUBSTITUTED IN POSITION 5, PHARMACEUTICAL COMPOSITION COMPRISING IT, INTERMEDIATE COMPOUNDS AND PREPARATION PROCESS THEREFOR
  申请人：A.C.R.A.F S.P.A. Aziende Chimiche Riunite Angelin Francesco

  公开号：US20130158269A1

  公开（公告）日：2013-06-20

  An (aza)indole derivative substituted in position 5, of formula (I) in which X, Y, Z, G1, G2, G3, R1, W, and R2 have the meanings given in the description, a pharmaceutical composition comprising it, and also intermediate compounds and a preparation process therefor.

  一种在5位取代的(aza)吲哚衍生物，其化学式为(I)，其中X、Y、Z、G1、G2、G3、R1、W和R2的含义如说明中所述，以及包含它的药物组合物，还包括中间化合物和其制备过程。