5-(4-Fluorophenyl)sulfanyl-2-nitroaniline | 378236-82-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(4-Fluorophenyl)sulfanyl-2-nitroaniline
• CAS: 378236-82-9
• 化学式: C₁₂H₉FN₂O₂S
• 分子量: 264.28
• InChiKey: RUOSDIBQMGSWHV-UHFFFAOYSA-N

物化性质

• 沸点：
  481.8±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-Fluorophenyl)sulfanyl-2-nitroaniline 在 sodium hydroxide 、 sodium tetrahydroborate 、 tin(ll) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 29.67h， 生成 methyl 5-(p-fluorophenylthio)-2-benzimidazolecarbamate
  参考文献：
  名称：

  三步高效合成和光谱测定5-[（o-，m-和对取代的苯硫基] -2-苯并咪唑氨基甲酸酯

  摘要：

  描述了通常具有新颖药理的5-[（o-，m-和对位取代）-苯硫基] -2-苯并咪唑氨基甲酸酯的制备和光谱性质，具有可能的药理活性作为抗蠕虫药；通过将5-甲基硫脲硫酸氯甲酸甲酯与溶于乙醇中的3,4-二氨基苯基取代的苯硫醚缩合和环化。ir证实了所有最终产品的结构；1 H-nmr，13 C-nmr和ms。

  DOI：

  10.1002/jhet.5570410220
• 作为产物：
  描述：

  2-硝基-5-氯苯胺 以82 %的产率得到5-(4-Fluorophenyl)sulfanyl-2-nitroaniline
  参考文献：
  名称：

  THIOBENZIMIDAZOLE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF AND USE THEREOF

  摘要：

  本发明涉及一种硫苯并咪唑衍生物或其药学上可接受的盐，以及一种用于预防或治疗癌症的组合物，所述组合物包含所述衍生物作为活性成分。本发明的硫苯并咪唑衍生物在给药于个体时，通过阻断癌细胞的细胞周期并诱导凋亡来表现出细胞毒性，因为所述衍生物在癌细胞中被激活后抑制微管蛋白聚合，因此，所述衍生物可用于预防或治疗癌症，尤其适用于预防或治疗三阴性乳腺癌。

  公开号：

  EP4230204A1

文献信息

• Indole derivatives with vascular damaging activity
  申请人：——

  公开号：US20030216356A1

  公开（公告）日：2003-11-20

  The invention provides a compound of Formula (I) wherein: R 1 and R 2 are independently selected from hydrogen, halogen, —CN, a hydrocarbyl group or a group of Formula (II); wherein W is aryl or a heterocyclic group, R 4 is independently select from hydrogen, halogen, —OH, amino, alkanoylamino, —OPO 3 H 2 , or a hydrocarbyl group, wherein the amino group is optionally substituted by an amino acid residue and the hydroxy group is optionally esterified or two R 4 groups together form an optionally substituted cyclic or heterocyclic group; X is selected from $M(y) S+—, +—O—+, —+S(O)+—, —+S(O 2 )+— and —+NH—; p is an integer from 0 to 4; and q is an integer from 1 to 4; R 3 and R 10 are independently selected from hydrogen, lower alkyl or a group of Formula (IV): wherein Y is selected from +NH+—, —$M(Y)O$M(Y)— or a bond; Z is selected from +NH+—, —+O&ngr;—, —+C(O)+— or a bond; r is an integer from 0 to 4; t is an integer from 0 to 1; R 6 is hydrogen, a hydrocarbyl group or a group of Formula (V): wherein n is an integer of from 1 to 6, and; R 7 and R 8 are independently selected from hydrogen or a hydrocarbyl group; and R 11 is hydrogen or lower alkyl; or a salt or solvate thereof; provided that: I) when R 1 is an unsubstituted phenylthio group (Ph—S—), R 2 is H, R 10 is H and R 11 is H then R 3 is neither H nor —C(O)—O—CH 2 CH 3 ; and ii) R 1 , R 2 and R 3 are not all hydrogen. Such compounds are predicted to cause the selective destruction of tumour vasculature. They may therefore be used to inhibit and/or reverse, and/or alleviate symptoms of angiogenesis and/or any disease state associated with angiogenesis. 1

  该发明提供了一个化合物，其化学式为（I），其中：R1和R2分别选自氢、卤素、—CN、烃基团或化学式（II）的基团；其中W为芳基或杂环基团，R4独立选择自氢、卤素、—OH、氨基、烷酰胺基、—OPO3H2或烃基团，其中氨基团可选择性地被氨基酸残基取代，羟基可选择性酯化，或两个R4基团共同形成一个可选择性取代的环状或杂环基团；X选自$M(y)S+—、+—O—+、—+S(O)+—、—+S(O2)+—和—+NH—；p为0至4之间的整数；q为1至4之间的整数；R3和R10独立选择自氢、较低烷基或化学式（IV）的基团：其中Y选自+NH+—、—$M(Y)O$M(Y)—或键；Z选自+NH+—、—+O&ngr;—、—+C(O)+—或键；r为0至4之间的整数；t为0或1之间的整数；R6为氢、烃基团或化学式（V）的基团：其中n为1至6之间的整数；R7和R8独立选择自氢或烃基团；R11为氢或较低烷基；或其盐或溶剂化合物；但要求：I）当R1为未取代的苯硫基团（Ph—S—）时，R2为H，R10为H且R11为H，则R3既不是H也不是—C(O)—O—CH2CH3；和II）R1、R2和R3不全为氢。预测这类化合物可能导致肿瘤血管的选择性破坏。因此，它们可以用于抑制和/或逆转和/或缓解血管生成及/或与血管生成相关的任何疾病状态的症状。
• INDOLE DERIVATIVES WITH VASCULAR DAMAGING ACTIVITY
  申请人：AstraZeneca AB

  公开号：EP1289952A1

  公开（公告）日：2003-03-12
• US4072696A
  申请人：——

  公开号：US4072696A

  公开（公告）日：1978-02-07
• US7030123B2
  申请人：——

  公开号：US7030123B2

  公开（公告）日：2006-04-18
• [EN] INDOLE DERIVATIVES WITH VASCULAR DAMAGING ACTIVITY<br/>[FR] DERIVES D'INDOLE POSSEDANT UNE ACTIVITE ENDOMMAGEANT LES VAISSEAUX SANGUINS
  申请人：ASTRAZENECA AB

  公开号：WO2001092224A1

  公开（公告）日：2001-12-06

  The invention provides a compound of Formula (I) wherein: R?1 and R2¿ are independently selected from hydrogen, halogen, -CN, a hydrocarbyl group or a group of Formula (II); wherein W is aryl or a heterocyclic group, R4 is independently selected from hydrogen, halogen, -OH, amino, alkanoylamino, -OPO¿3?H2, or a hydrocarbyl group, wherein the amino group is optionally substituted by an amino acid residue and the hydroxy group is optionally esterified or two R?4¿ groups together form an optionally substituted cyclic or heterocyclic group; X is selected from $M(y) S -, -O- , - S(O) -, - S(O¿2?) - and - NH -; p is an integer from 0 to 4; and q is an integer from 1 to 4; R?3 and R10¿ are independently selected from hydrogen, lower alkyl or a group of Formula (IV): wherein Y is selected from NH -, - $M(Y)O$M(Y)- or a bond; Z is selected from NH -, - Oω-, - C(O) - or a bond; r is an integer from 0 to 4; t is an integer from 0 to 1; R6 is hydrogen, a hydrocarbyl group or a group of Formula (V): wherein n is an integer of from 1 to 6, and; R?7 and R8¿ are independently selected from hydrogen or a hydrocarbyl group; and R11 is hydrogen or lower alkyl; or a salt or solvate thereof; provided that: I) when R1 is an unsubstituted phenylthio group (Ph-S-), R2 is H, R10 is H and R11 is H then R3 is neither H nor- C(O)-O-CH¿2?CH3; and ii) R?1, R2 and R3¿ are not all hydrogen. Such compounds are predicted to cause the selective destruction of tumour vasculature. They may therefore be used to inhibit and/or reverse, and/or alleviate symptoms of angiogenesis and/or any disease state associated with angiogenesis.