{3-[hydroxy(pentafluorobenzoyl)amino]propyl}phosphonic acid | 954105-19-2

• 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: {3-[hydroxy(pentafluorobenzoyl)amino]propyl}phosphonic acid
• 英文别名: 3-[Hydroxy-(2,3,4,5,6-pentafluorobenzoyl)amino]propylphosphonic acid
• CAS: 954105-19-2
• 化学式: C₁₀H₉F₅NO₅P
• 分子量: 349.151
• InChiKey: VTGIACKHRHKZMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.1
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  {3-[(benzyloxy)(pentafluorobenzoyl)amino]propyl}phosphonic acid dibenzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以96%的产率得到{3-[hydroxy(pentafluorobenzoyl)amino]propyl}phosphonic acid
  参考文献：
  名称：

  新型脱氧木酮糖磷酸还原异构酶抑制剂：具有大量酰基残基的磷米霉素衍生物

  摘要：

  1 - 脱氧 - D - 木酮糖 - 5 - 磷酸还原异构酶 (Dxr) 代表类异戊二烯生物合成的非甲羟戊酸途径的必需酶。使用 fosmidomycin 作为 Dxr 的特异性抑制剂，这种酶以前被验证为治疗疟疾和细菌感染的靶点。fosmidomycin 的甲酰基残基被宽敞的酰基残基取代产生了在微摩尔范围内有活性的抑制剂。正如柔性对接所预测的那样，获得了在酰基残基中适当放置的羰基与位于酶的柔性催化环中的 Met214 的主链 NH 之间形成氢键的证据。

  DOI：

  10.1002/ardp.200700149

文献信息

• INHIBITION OF ISOPRENOID BIOSYNTHETIC PATHWAYS TO TREAT NEUROINFLAMMATORY DISORDERS
  申请人：TABACZYNSKI David A.

  公开号：US20160303146A1

  公开（公告）日：2016-10-20

  This invention provides methods and pharmaceutical compositions that can treat neuroinflammatory disease by reducing the production of pyrophosphate intermediates produced during the biosynthesis of isoprenoids. The pyrophosphate compounds being inhibited are normally produced through the mevalonate and non-mevalonate pathways of the host vertebrate organisms and their symbiotic and pathogenic microorganisms. The methods involve administering to a patient an inhibitor of the mevalonate-dependent pathway, an inhibitor of the non-mevalonate pathway, or combination of such inhibitors.
• INHIBITION OF ISOPRENOID BIOSYNTHETIC PATHWAYS TO TREAT AUTOIMMUNE DISORDERS
  申请人：TABACZYNSKI David A.

  公开号：US20160375041A1

  公开（公告）日：2016-12-29

  The invention provides methods and pharmaceutical compositions that can treat autoimmune disease by reducing the production of pyrophosphate intermediates produced during the biosynthesis of isoprenoids. The pyrophosphate compounds being inhibited are normally produced through the mevalonate and non-mevalonate pathways of the host vertebrate organisms and their symbiotic and pathogenic microorganisms. The methods involve administering to a patient an inhibitor of the mevalonate-dependent pathway, an inhibitor of the non-mevalonate pathway, or combination of such inhibitors.
• [EN] INHIBITION OF ISOPRENOID BIOSYNTHETIC PATHWAYS TO TREAT AUTOIMMUNE DISORDERS<br/>[FR] INHIBITION DE VOIES DE BIOSYNTHÈSE D'ISOPRÉNOÏDES POUR TRAITER DES TROUBLES AUTO-IMMUNS
  申请人：TABACZYNSKI DAVID A

  公开号：WO2015084721A1

  公开（公告）日：2015-06-11

  The invention provides methods and pharmaceutical compositions that can treat autoimmune disease by reducing the production of pyrophosphate intermediates produced during the biosynthesis of isoprenoids. The pyrophosphate compounds being inhibited are normally produced through the mevalonate and non-mevalonate pathways of the host vertebrate organisms and their symbiotic and pathogenic microorganisms. The methods involve administering to a patient an inhibitor of the mevalonate-dependent pathway, an inhibitor of the non-mevalonate pathway, or combination of such inhibitors.
• [EN] INHIBITION OF ISOPRENOID BIOSYNTHETIC PATHWAYS TO TREAT NEUROINFLAMMATORY DISORDERS<br/>[FR] INHIBITION DE VOIES DE BIOSYNTHÈSE D'ISOPRÉNOÏDES POUR TRAITER DES TROUBLES NEURO-INFLAMMATOIRES
  申请人：TABACZYNSKI DAVID A

  公开号：WO2015089349A1

  公开（公告）日：2015-06-18

  This invention provides methods and pharmaceutical compositions that can treat neuroinflammatory disease by reducing the production of pyrophosphate intermediates produced during the biosynthesis of isoprenoids. The pyrophosphate compounds being inhibited are normally produced through the mevalonate and non-mevalonate pathways of the host vertebrate organisms and their symbiotic and pathogenic microorganisms. The methods involve administering to a patient an inhibitor of the mevalonate-dependent pathway, an inhibitor of the non-mevalonate pathway, or combination of such inhibitors.
• Novel Deoxyxylulosephosphate-Reductoisomerase Inhibitors: Fosmidomycin Derivatives with Spacious Acyl Residues
  作者：Regina Ortmann、Jochen Wiesner、Katrin Silber、Gerhard Klebe、Hassan Jomaa、Martin Schlitzer

  DOI：10.1002/ardp.200700149

  日期：2007.9

  enzyme of the mevalonate‐independent pathway of the isoprenoid biosynthesis. Using fosmidomycin as a specific inhibitor of Dxr, this enzyme was previously validated as target for the treatment of malaria and bacterial infections. The replacement of the formyl residue of fosmidomycin by spacious acyl residues yielded inhibitors active in the micromolar range. As predicted by flexible docking, evidence was

  1 - 脱氧 - D - 木酮糖 - 5 - 磷酸还原异构酶 (Dxr) 代表类异戊二烯生物合成的非甲羟戊酸途径的必需酶。使用 fosmidomycin 作为 Dxr 的特异性抑制剂，这种酶以前被验证为治疗疟疾和细菌感染的靶点。fosmidomycin 的甲酰基残基被宽敞的酰基残基取代产生了在微摩尔范围内有活性的抑制剂。正如柔性对接所预测的那样，获得了在酰基残基中适当放置的羰基与位于酶的柔性催化环中的 Met214 的主链 NH 之间形成氢键的证据。