[3-(Pyrrole-1-sulfonyl)-thiophen-2-ylmethyl]-phosphonic acid diethyl ester | 184040-86-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: [3-(Pyrrole-1-sulfonyl)-thiophen-2-ylmethyl]-phosphonic acid diethyl ester
• 英文别名: 1-[2-(Diethoxyphosphorylmethyl)thiophen-3-yl]sulfonylpyrrole；1-[2-(diethoxyphosphorylmethyl)thiophen-3-yl]sulfonylpyrrole
• CAS: 184040-86-6
• 化学式: C₁₃H₁₈NO₅PS₂
• 分子量: 363.395
• InChiKey: NCYWHAZFZZNFDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [3-(Pyrrole-1-sulfonyl)-thiophen-2-ylmethyl]-phosphonic acid diethyl ester 在 氢氧化钾 、 五氯化磷 、 水 、 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 2-((E)-2-Benzo[1,3]dioxol-5-yl-vinyl)-thiophene-3-sulfonyl chloride
  参考文献：
  名称：

  Amide bond surrogates: A study in thiophenesulfonamide based endothelin receptor antagonists

  摘要：

  The potential proteolytic instability of the amide bond present in some ETA selective thiophenesulfonamide endothelin antagonists exemplified by TBC-10708 led us to investigate the replacement of this moiety with stable amide bond surrogates such as a trans double bond and an ethylene spacer. The effect of these replacements on the binding affinity is described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00133-9
• 作为产物：
  描述：

  N-[(2-bromomethyl)thiophene-3-sulfonyl]pyrrole 、 亚磷酸三乙酯 以83%的产率得到[3-(Pyrrole-1-sulfonyl)-thiophen-2-ylmethyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Amide bond surrogates: A study in thiophenesulfonamide based endothelin receptor antagonists

  摘要：

  The potential proteolytic instability of the amide bond present in some ETA selective thiophenesulfonamide endothelin antagonists exemplified by TBC-10708 led us to investigate the replacement of this moiety with stable amide bond surrogates such as a trans double bond and an ethylene spacer. The effect of these replacements on the binding affinity is described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00133-9

文献信息

• Biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin
  申请人：——

  公开号：US20020095041A1

  公开（公告）日：2002-07-18

  Biphenylsulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, bicyclic or tricyclic carbon or heterocyclic ring biphenylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.

  提供了二苯基磺胺类化合物和调节或改变内皮素家族肽活性的方法。具体包括使用双环或三环碳或杂环环二苯基磺胺类化合物的方法，通过将该磺胺类化合物与内皮素受体接触来抑制内皮素肽与内皮素受体的结合。还提供了通过给予有效剂量的这些磺胺类化合物或其前药来治疗内皮素介导的疾病的方法，这些化合物能够抑制或增加内皮素的活性。
• US6613804B2
  申请人：——

  公开号：US6613804B2

  公开（公告）日：2003-09-02
• Amide bond surrogates: A study in thiophenesulfonamide based endothelin receptor antagonists
  作者：B. Raju、Ilya Okun、Fiona Stavros、Ming Fai Chan

  DOI：10.1016/s0960-894x(97)00133-9

  日期：1997.1

  The potential proteolytic instability of the amide bond present in some ETA selective thiophenesulfonamide endothelin antagonists exemplified by TBC-10708 led us to investigate the replacement of this moiety with stable amide bond surrogates such as a trans double bond and an ethylene spacer. The effect of these replacements on the binding affinity is described. (C) 1997 Elsevier Science Ltd.