N-(4-cyano-2-chlorophenyl)methanesulfonamide | 865878-58-6

• 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-chlorophenyl)methanesulfonamide
• 英文别名: N-(2-chloro-4-cyanophenyl)methanesulfonamide
• CAS: 865878-58-6
• 化学式: C₈H₇ClN₂O₂S
• 分子量: 230.675
• InChiKey: PTYFZRSNJYYBRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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-chlorophenyl)methanesulfonamide 在 硼烷四氢呋喃络合物 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以99%的产率得到N-(4-aminomethyl-2-chloro-phenyl)-methanesulfonamide hydrochloride
  参考文献：
  名称：

  Synthesis and structural optimization of multiple H-bonding region of diarylalkyl (thio)amides as novel TRPV1 antagonists

  摘要：

  Structural optimization of multiple H-bonding region and structure-activity relationship of diarylalkyl amides/thioamides as novel TRPV1 antagonists are described. In particular, we identified amide 34o and thioamides 35o and 35r, of which antagonistic activities were highly enhanced by an incorporation of cyano or vinyl-substituent to the multiple H-bonding region. They exhibited potent Ca-45(2+) uptake inhibitions in rat DRG neuron with IC(50)s of 25, 32 and 28 nM, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.043
• 作为产物：
  描述：

  2-氯-4-碘苯胺 在 吡啶 、 四(三苯基膦)钯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 N-(4-cyano-2-chlorophenyl)methanesulfonamide
  参考文献：
  名称：

  Novel Potent Antagonists of Transient Receptor Potential Channel, Vanilloid Subfamily Member 1:  Structure−Activity Relationship of 1,3-Diarylalkyl Thioureas Possessing New Vanilloid Equivalents

  摘要：

  Recently, 1,3-diarylalkyl thioureas have merged as one of the promising nonvanilloid TRPV1 antagonists possessing excellent therapeutic potential in pain regulation. In this paper, the full structure-activity relationship for TRPV1 antagonism of a novel series of 1,3-diarylalky thioureas is reported. Exploration of the structure- activity relationship, by systemically modulating three essential pharmacophoric regions, led to six examples of 1,3-dibenzyl thioureas, which exhibit Ca2+ uptake inhibition in rat DRG neuron with IC50 between 10 and 100 nM.

  DOI：

  10.1021/jm0502790

文献信息

• Mild hypervalent iodine mediated oxidative nitration of N-aryl sulfonamides
  作者：Ulrich Kloeckner、Boris J. Nachtsheim

  DOI：10.1039/c4cc04738a

  日期：——

  An oxidative and acid-free method for the nitration of N-aryl sulfonamides has been developed using a combination of sodium nitrite as cheap and easy to handle NO2-source and the hypervalent iodine reagent PIFA as stoichiometric oxidant. Under very mild reaction conditions, the desired mononitrated aryl sulfonamides were isolated in up to 87% yield. This is the first example of an iodane-mediated oxidative nitration.

  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。
• Substituted N-sulfonylaminobenzyl-2-phenoxyacetamide compounds as VR1 receptor agonists
  申请人：Inoue Tadashi

  公开号：US20060100460A1

  公开（公告）日：2006-05-11

  This invention provides a compound of the formula (I): wherein R 1 represents a (C 1 -C 6 )alkyl group; R 2 represents a hydrogen atom, a halogen atom, a hydroxy group, a (C 1 -C 6 ) alkyl group or a (C 1 -C 6 ) alkoxy group; R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom, a (C 1 -C 6 ) alkyl, or a halogen atom; R 7 represents a hydrogen atom, a halogen atom, a hydroxy group, a (C 1 -C 6 ) alkyl group optionally substituted with a piperidino group, a (C- 1 -C 6 )alkoxy group optionally substituted with a 3-7 membered cycloalkyl ring, a hydroxy(C 1 -C 6 )alkoxy group, a (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkoxy group, a halo (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkylthio group, a (C 1 -C 6 )alkylsulfinyl group or a (C 1 -C 6 )alkylsulfonyl group; R 5 represents a (C 1 -C 6 )alkyl group, a halo(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a hydroxy(C 1 -C 6 )alkoxy group, a (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl group or a (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkoxy group; or R 7 and R 8 , when adjacent to each other, taken together with the carbon atoms to which they are attached form a 5-8 membered carbocyclic or heterocyclic ring, wherein the carbocyclic ring or the heterocyclic ring is unsubstituted or substituted with one or more substituents selected from the group consisting of a hydroxy group, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group and a hydroxy(C 1 -C 6 )alkyl group; and R 9 represents a hydrogen atom or a halogen atom; or a pharmaceutically acceptable salt or solvate thereof. These compounds are useful for the treatment of disease conditions caused by overactivation of VR1 receptor, such as pain or the like in mammalian. The present invention also provides a pharmaceutical composition comprising the compound of formula (I).

  这项发明提供了一种化合物，其化学式为（I）：其中R1代表（C1-C6）烷基基团；R2代表氢原子、卤原子、羟基、（C1-C6）烷基基团或（C1-C6）氧烷基基团；R3、R4、R5和R6分别独立地代表氢原子、（C1-C6）烷基或卤原子；R7代表氢原子、卤原子、羟基、（C1-C6）烷基基团，可选地取代有哌啶基团的（C1-C6）烷基基团，可选地取代有3-7个成员的环烷基环的（C-1-C6）氧烷基基团，羟基（C1-C6）氧烷基基团，（C1-C6）氧烷基（C1-C6）烷基基团，（C1-C6）氧烷基（C1-C6）氧烷基基团，卤代（C1-C6）烷基基团，（C1-C6）烷基硫基基团，（C1-C6）烷基亚硫基基团或（C1-C6）烷基砜基基团；R8代表（C1-C6）烷基基团，卤代（C1-C6）烷基基团，（C1-C6）氧烷基基团，羟基（C1-C6）氧烷基基团，（C1-C6）氧烷基（C1-C6）烷基基团或（C1-C6）氧烷基（C1-C6）氧烷基基团；或者R7和R8，当相邻时，与它们连接的碳原子一起形成一个5-8成员的脂环或杂环环，其中脂环或杂环环未取代或取代有一个或多个选自羟基、（C1-C6）烷基、（C1-C6）氧烷基和羟基（C1-C6）烷基的取代基；R9代表氢原子或卤原子；或其药学上可接受的盐或溶剂。这些化合物可用于治疗由VR1受体过度激活引起的疾病症状，如哺乳动物中的疼痛等。本发明还提供了一种包含化合物（I）的药物组成物。
• SUBSTITUTED N-SULFONYLAMINOBENZYL-2-PHENOXY ACETAMIDE COMPOUNDS
  申请人：Pfizer, Inc.

  公开号：EP1824837B1

  公开（公告）日：2008-08-13
• US7214824B2
  申请人：——

  公开号：US7214824B2

  公开（公告）日：2007-05-08
• Novel Potent Antagonists of Transient Receptor Potential Channel, Vanilloid Subfamily Member 1:  Structure−Activity Relationship of 1,3-Diarylalkyl Thioureas Possessing New Vanilloid Equivalents
  作者：Young-Ger Suh、Yong-Sil Lee、Kyung-Hoon Min、Ok-Hui Park、Jin-Kwan Kim、Ho-Sun Seung、Seung-Yong Seo、Bo-Young Lee、Yeon-Hee Nam、Kwang-Ok Lee、Hee-Doo Kim、Hyeung-Geun Park、Jeewoo Lee、Uhtaek Oh、Ju-Ok Lim、Sang-Uk Kang、Min-Jung Kil、Jae-yeon Koo、Song Seok Shin、Yung-Hyup Joo、Jin Kwan Kim、Yeon-Su Jeong、Sun-Young Kim、Young-Ho Park

  DOI：10.1021/jm0502790

  日期：2005.9.1

  Recently, 1,3-diarylalkyl thioureas have merged as one of the promising nonvanilloid TRPV1 antagonists possessing excellent therapeutic potential in pain regulation. In this paper, the full structure-activity relationship for TRPV1 antagonism of a novel series of 1,3-diarylalky thioureas is reported. Exploration of the structure- activity relationship, by systemically modulating three essential pharmacophoric regions, led to six examples of 1,3-dibenzyl thioureas, which exhibit Ca2+ uptake inhibition in rat DRG neuron with IC50 between 10 and 100 nM.