{[(4-fluorophenyl)sulfonyl]amino}-5-methylbenzoicacid | 1026661-33-5

• 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: {[(4-fluorophenyl)sulfonyl]amino}-5-methylbenzoicacid
• 英文别名: 2-[(4-fluorophenyl)sulfonylamino]-5-methylbenzoic acid
• CAS: 1026661-33-5
• 化学式: C₁₄H₁₂FNO₄S
• 分子量: 309.318
• InChiKey: PJOURFSUIKLILD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基-5-甲基苯甲酸 、 4-氟苯磺酰氯 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 6.0h， 以0.3 g的产率得到{[(4-fluorophenyl)sulfonyl]amino}-5-methylbenzoicacid
  参考文献：
  名称：

  Potent anti-prostate cancer agents derived from a novel androgen receptor down-regulating agent

  摘要：

  The search for novel androgen receptor (AR) down-regulating agents by catalyst HipHop pharmacophore modeling led to the discovery of some lead molecules. Unexpectedly, the effect of these leads on human prostate cancer LNCaP cell viability did not correlate with the ability of the compounds to cause down-regulation of AR protein expression. Through rational synthetic optimization of the lead compound (BTB01434), we have discovered a series of novel substituted diaryl molecules as potent anti-prostate cancer agents. Some compounds (1-6) were shown to be extremely potent inhibitors of LNCaP cell viability with GI(50) values in the nanomolar range (1.45-83 nM). The most potent compound (4-methylphenyl)[(4-methylphenyl) sulfonyl] amine (5) with a GI(50) value of 1.45 nM is 27,000 times more potent than our lead compound BTB01434 (GI(50) = 39.8 mu M). In addition, some of the compounds exhibited modest anti-androgenic activities and one was also a potent inhibitor (GI(50) = 850 nM) of PC-3 (AR-null) cell growth. A clear structure-activity relationship (SAR) has been established for activity against LNCaP cells, where potent molecules possess two substituted/unsubstituted aromatic rings connected through a sulfonamide linker. These novel compounds are strong candidates for development for the treatment of hormone-sensitive and importantly hormone-refractory prostate cancers in humans. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.031
• 作为试剂：
  描述：

  2-氨基-5-甲基苯甲酸 、 4-氟苯磺酰氯 、 disodium;carbonate 、 在 {[(4-fluorophenyl)sulfonyl]amino}-5-methylbenzoicacid 、 水 作用下， 以 水 为溶剂， 以to give 12 (0.44 g, 85.42%)的产率得到{[(4-fluorophenyl)sulfonyl]amino}-5-methylbenzoicacid
  参考文献：
  名称：

  Anti-cancer agents and androgen inhibition activity compound

  摘要：

  从已知的天然产物雄激素受体下调剂（ARDAs）中开发了一种定性的3D药效团模型（常见特征基模型或Catalyst HipHop算法）。这种3D药效团模型被用作虚拟筛选新ARDAs化合物的模板。这些化合物和能够强烈抑制人前列腺LNCaP细胞生长的化合物一起被用于组合物和抑制癌症细胞增殖的方法及预防或治疗癌症（包括前列腺癌）的方法。

  公开号：

  US07960435B2

文献信息

• ANTI-CANCER AGENTS AND ANDROGEN INHIBITION ACTIVITY COMPOUND
  申请人：Njar Vincent C. O.

  公开号：US20100113600A1

  公开（公告）日：2010-05-06

  A qualitative 3D pharmacophore model (a common feature based model or Catalyst HipHop algorithm) developed from well-known natural product androgen receptor down-regulating agents (ARDAs). The 3D pharmacophore model is used as a template in virtual screening compounds for new ARDAs. ARDA compounds and compounds that strongly inhibit the growth of human prostate LNCaP cells. The compounds may be used in compositions and methods of inhibiting cell proliferation of a cancer and methods of preventing or treating cancer, including prostate cancer.

  使用常见特征基模型或Catalyst HipHop算法从著名的天然产物雄激素受体下调剂（ARDAs）中开发出一种定性的3D药效团模型。该3D药效团模型被用作模板，筛选新的ARDAs化合物。ARDAs化合物和强烈抑制人前列腺LNCaP细胞生长的化合物。这些化合物可用于抑制癌症细胞增殖的组合物和方法，以及预防或治疗癌症，包括前列腺癌的方法。
• US7960435B2
  申请人：——

  公开号：US7960435B2

  公开（公告）日：2011-06-14
• [EN] ANTI-CANCER AGENTS AND ANDROGEN INHIBITION ACTIVITY COMPOUND<br/>[FR] AGENTS ANTI-CANCER ET COMPOSÉ INHIBANT L'ACTIVITÉ ANDROGÈNE
  申请人：UNIV MARYLAND

  公开号：WO2008076918A2

  公开（公告）日：2008-06-26

  (EN) A qualitative 3D pharmacophore model (a common feature based model or Catalyst HipHop algorithm) developed from well-known natural product androgen receptor down-regulating agents (ARDAs). The 3D pharmacophore model is used as a template in virtual screening compounds for new ARDAs. ARDA compounds and compounds that strongly inhibit the growth of human prostate LNCaP cells. The compounds may be used in compositions and methods of inhibiting cell proliferation of a cancer and methods of preventing or treating cancer, including prostate cancer.(FR) L'invention concerne un modèle 3D qualitatif de pharmacophore (un modèle fondé sur une fonctionnalité courante ou un algorithme Catalyst HipHop) développé à partir d'agents rétro-régulateurs du récepteur androgène (ARDA) naturels. Le modèle 3D de pharmacophore est utilisé en tant que modèle pour le criblage virtuel de composés dans le but d'identifier de nouveaux ARDA. L'invention concerne également des composés ARDA et des composés qui inhibent fortement la croissance des cellules LNCaP de la prostate humaine. Les composés peuvent être utilisés dans des compositions et des procédés pour inhiber la prolifération cellulaire d'un cancer et dans des procédés de prévention ou de traitement du cancer, notamment du cancer de la prostate.
• Potent anti-prostate cancer agents derived from a novel androgen receptor down-regulating agent
  作者：Puranik Purushottamachar、Aakanksha Khandelwal、Tadas S. Vasaitis、Robert D. Bruno、Lalji K. Gediya、Vincent C.O. Njar

  DOI：10.1016/j.bmc.2008.02.031

  日期：2008.4.1

  The search for novel androgen receptor (AR) down-regulating agents by catalyst HipHop pharmacophore modeling led to the discovery of some lead molecules. Unexpectedly, the effect of these leads on human prostate cancer LNCaP cell viability did not correlate with the ability of the compounds to cause down-regulation of AR protein expression. Through rational synthetic optimization of the lead compound (BTB01434), we have discovered a series of novel substituted diaryl molecules as potent anti-prostate cancer agents. Some compounds (1-6) were shown to be extremely potent inhibitors of LNCaP cell viability with GI(50) values in the nanomolar range (1.45-83 nM). The most potent compound (4-methylphenyl)[(4-methylphenyl) sulfonyl] amine (5) with a GI(50) value of 1.45 nM is 27,000 times more potent than our lead compound BTB01434 (GI(50) = 39.8 mu M). In addition, some of the compounds exhibited modest anti-androgenic activities and one was also a potent inhibitor (GI(50) = 850 nM) of PC-3 (AR-null) cell growth. A clear structure-activity relationship (SAR) has been established for activity against LNCaP cells, where potent molecules possess two substituted/unsubstituted aromatic rings connected through a sulfonamide linker. These novel compounds are strong candidates for development for the treatment of hormone-sensitive and importantly hormone-refractory prostate cancers in humans. (C) 2008 Elsevier Ltd. All rights reserved.
• Anti-cancer agents and androgen inhibition activity compound
  申请人：University of Maryland, Baltimore

  公开号：US07960435B2

  公开（公告）日：2011-06-14

  A qualitative 3D pharmacophore model (a common feature based model or Catalyst HipHop algorithm) developed from well-known natural product androgen receptor down-regulating agents (ARDAs). The 3D pharmacophore model is used as a template in virtual screening compounds for new ARDAs. ARDA compounds and compounds that strongly inhibit the growth of human prostate LNCaP cells. The compounds may be used in compositions and methods of inhibiting cell proliferation of a cancer and methods of preventing or treating cancer, including prostate cancer.

  从已知的天然产物雄激素受体下调剂（ARDAs）中开发了一种定性的3D药效团模型（常见特征基模型或Catalyst HipHop算法）。这种3D药效团模型被用作虚拟筛选新ARDAs化合物的模板。这些化合物和能够强烈抑制人前列腺LNCaP细胞生长的化合物一起被用于组合物和抑制癌症细胞增殖的方法及预防或治疗癌症（包括前列腺癌）的方法。