N-(4-cyano-2-iodophenyl)methanesulfonamide | 381210-41-9

• 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-(4-cyano-2-iodophenyl)methanesulfonamide
• 英文别名: N-mesyl-3-iodobenzonitrile
• CAS: 381210-41-9
• 化学式: C₈H₇IN₂O₂S
• 分子量: 322.126
• InChiKey: OZQPTRWBESGVEG-UHFFFAOYSA-N

物化性质

• 沸点：
  406.4±55.0 °C(Predicted)
• 密度：
  1.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-cyano-2-iodophenyl)methanesulfonamide 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 TEA 作用下， 以 甲醇 为溶剂， 生成 2-(2,2'-Dimethoxy-biphenyl-3-yl)-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Factor VIIa inhibitors: A prodrug strategy to improve oral bioavailability

  摘要：

  We have developed a series of potent and selective factor VIIa inhibitors based on the 2-[5-(5-carbamimidoyl-1H-benzoimidazol-2-yl)-6-hydroxy-biphenyl-3-yl]-succinic acid scaffold. These amidine-containing compounds have low oral bioavailability. Herein, we describe our efforts to improve the oral bioavailability of the parent amidine via a prodrug strategy where the amidine basicity and polarity were reduced with either an alkoxy-amidine or a carbamate prodrug. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.039

文献信息

• 2- [5- (5-carbamimidoyl-1H-heteroaryl)-6-hydroxybiphenyl-3-yl]-succinic acid derivatives as factor viia inhibitors
  申请人：Axys Pharmaceuticals, Inc.

  公开号：US20030114457A1

  公开（公告）日：2003-06-19

  The present invention relates to novel inhibitors of Factors VIIa, IXa, Xa, XIa, in particular Factor VIIa, pharmaceutical compositions comprising these inhibitors, and methods for using these inhibitors for treating or preventing thromboembolic disorders. Processes for preparing these inhibitors are also disclosed.

  本发明涉及新型因子VIIa、IXa、Xa、XIa的抑制剂，特别是因子VIIa，包括这些抑制剂的药物组合物，以及利用这些抑制剂治疗或预防血栓栓塞性疾病的方法。还公开了制备这些抑制剂的方法。
• 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。
• Sequential coupling/desilylation–coupling/cyclization in a single pot under Pd/C–Cu catalysis: Synthesis of 2-(hetero)aryl indoles
  作者：R. Mohan Rao、Upendar Reddy CH、Alinakhi、Naveen Mulakayala、Mallika Alvala、M. K. Arunasree、Rajamohan R. Poondra、Javed Iqbal、Manojit Pal

  DOI：10.1039/c0ob01161d

  日期：——

  A new one-pot synthesis of 2-(hetero)aryl indolesvia sequential C–C coupling followed by C–Si bond cleavage and a subsequent tandem C–C/C–N bond forming reaction is described. A variety of functionalized indole derivatives were prepared by conducting this four step reaction under Pd/C–Cu catalysis. The methodology involved coupling of (trimethylsilyl)acetylene with iodoarenes in the presence of 10%

  描述了通过一连串的C-C偶联，随后的C-Si键断裂和随后的串联C-C / C-N键形成反应的新的一锅法合成2-（杂）芳基吲哚的方法。通过在Pd / C-Cu催化下进行此四步反应，可以制备各种功能化的吲哚衍生物。该方法涉及耦合（三甲基甲硅烷基）乙炔与在10％的存在的Pd / C-的CuI-PPH iodoarenes 3和三乙胺 在 甲醇，然后在水溶液中用K 2 CO 3处理反应混合物甲醇，最后与邻碘碘化物偶联。给出了合成的吲哚衍生物的单晶X射线数据。描述了该方法的应用，合成化合物的体外药理特性以及对接研究。
• 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。
• New Synthetic Method for Indole-2-carboxylate and Its Application to the Total Synthesis of Duocarmycin SA
  作者：Kou Hiroya、Shigemitsu Matsumoto、Takao Sakamoto

  DOI：10.1021/ol0489548

  日期：2004.8.1

  aryl halides and methyl propiolate were investigated. The electron-withdrawing groups on the aromatic ring are essential for producing the methyl indole-2-carboxylate derivatives. On the other hand, the presence of an extra methyl propiolate and Pd(PPh3)4 were required to provide an efficient catalytic system for the cyclization reactions. This reaction was used for the total synthesis of duocarmycin

  研究了芳基卤化物与丙酸甲酯之间的顺序偶联和环化反应。芳环上的吸电子基团对于生产吲哚-2-羧酸甲酯衍生物是必不可少的。另一方面，需要额外的丙酸甲酯和Pd（PPh3）4的存在才能为环化反应提供有效的催化体系。该反应用于杜卡霉素SA的全合成。