3-chloropropylphosphonic acid | 13317-09-4

• 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-chloropropylphosphonic acid
• CAS: 13317-09-4
• 化学式: C₃H₈ClO₃P
• mdl: MFCD16877721
• 分子量: 158.521
• InChiKey: SUAATVSKKHVVJP-UHFFFAOYSA-N

物化性质

• 熔点：
  95-97.5 °C
• 沸点：
  337.2±44.0 °C(Predicted)
• 密度：
  1.459±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloropropylphosphonic acid 在 五氯化磷 作用下， 以 氯仿 为溶剂， 生成 dichloride of 3-chloropropylphosphonic acid
  参考文献：
  名称：

  Helferich,B.; Curtius,U., Justus Liebigs Annalen der Chemie, 1962, vol. 655, p. 59 - 69

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl (3-chloropropyl)phosphonate 在 盐酸 作用下， 生成 3-chloropropylphosphonic acid
  参考文献：
  名称：

  Phosphonic Acids. V.¹ An Improved Method for the Preparation of Sodium Diethyl Phosphonate and a Study of its Comparative Reactivity with Alkyl Halides and p-Toluenesulfonates²

  摘要：

  DOI：

  10.1021/ja01567a068

文献信息

• NOVEL 5-SUBSTITUTED BENZIMIDAZOLIUM COMPOUNDS
  申请人：KLEY Joerg

  公开号：US20150018313A1

  公开（公告）日：2015-01-15

  The present invention relates to compounds of general formula (I) and the tautomers and the salts thereof, particularly the pharmaceutically acceptable salts thereof with inorganic or organic acids and bases, which have valuable pharmacological properties, particularly an inhibitory effect on epithelial sodium channels, the use thereof for the treatment of diseases, particularly diseases of the lungs and airways.

  本发明涉及一般式（I）的化合物，以及其互变异构体和盐，特别是其与无机或有机酸和碱形成的药用可接受盐，具有有价值的药理特性，特别是对上皮钠通道具有抑制作用，以及其用于治疗疾病，特别是肺部和气道疾病的用途。
• [EN] NOVEL 5-SUBSTITUTED BENZIMIDAZOLIUM COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS BENZIMIDAZOLIUM SUBSTITUÉS EN POSITION 5
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2015007516A1

  公开（公告）日：2015-01-22

  The present invention relates to compounds of general formula (I) and the tautomers and the salts thereof, particularly the pharmaceutically acceptable salts thereof with inorganic or organic acids and bases, which have valuable pharmacological properties, particularly an inhibitory effect on epithelial sodium channels, the use thereof for the treatment of diseases, particularly diseases of the lungs and airways.

  本发明涉及一般式（I）的化合物，以及其互变异构体和盐，特别是其与无机或有机酸和碱形成的药用可接受盐，具有有价值的药理特性，特别是对上皮钠通道具有抑制作用，以及其用于治疗疾病，特别是肺部和气道疾病。
• [EN] SUBSTITUTED BENZIMIDAZOLIUM COMPOUNDS USEFUL IN THE TREATMENT OF RESPIRATORY DISEASES<br/>[FR] COMPOSÉS SUBTITUÉS À BASE DE BENZIMIDAZOLIUM UTILISABLES DANS LE TRAITEMENT DE MALADIES RESPIRATOIRES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2016113167A1

  公开（公告）日：2016-07-21

  The present invention relates to compounds of formula (I), or the tautomers or pharmacologically acceptable acid addition salts thereof, characterized by a topological polar surface area value (TPSA) of at least 145, wherein R1, R2, R3, R4, X, and Z- have one of the meanings as defined in the specification, to the use of compounds of formula (I) as a medicament, to pharmaceutical composition comprising at least one compound of formula (I), as well as to medicament combinations containing one or more compounds of formula (I).

  本发明涉及公式（I）的化合物，或其互变异构体或药理学上可接受的酸盐，其具有至少145的拓扑极性表面积值（TPSA），其中R1、R2、R3、R4、X和Z-具有规范中定义的含义之一，以及将公式（I）的化合物用作药物的用途，包括至少一种公式（I）的化合物的药物组合物，以及含有一种或多种公式（I）的化合物的药物组合物。
• Synthesis of Isosteric Phosphono Analogs of Biologically Active Alkylphosphocholines
  作者：Jörg T. Kley、Clemens Unger、Ulrich Massing

  DOI：10.1007/pl00010153

  日期：1998.2

  We describe a high yield reaction sequence for the conversion of long chain alcohols into 3-(trimethylammonio)propylphosphonates. The products are phospholipase D stable isosteric phosphono analogs of the respective alkylphosphocholines. The key step is the esterification of 3-chloropropylphosphonic acid with the respective long chain alcohols using DCC/DMAP. Deprotection and various acylations of 2-hydroxy and 2-amino groups following the introduction of the headgroup are described.
• Autotaxin structure–activity relationships revealed through lysophosphatidylcholine analogs
  作者：E. Jeffrey North、Daniel A. Osborne、Peter K. Bridson、Daniel L. Baker、Abby L. Parrill

  DOI：10.1016/j.bmc.2009.03.030

  日期：2009.5

  Autotaxin (ATX) catalyzes the hydrolysis of lysophosphatidylcholine (LPC) to form the bioactive lipid lysophosphatidic acid (LPA). LPA stimulates cell proliferation, cell survival, and cell migration and is involved in obesity, rheumatoid arthritis, neuropathic pain, atherosclerosis and various cancers, suggesting that ATX inhibitors have broad therapeutic potential. Product feedback inhibition of ATX by LPA has stimulated structure-activity studies focused on LPA analogs. However, LPA displays mixed mode inhibition, indicating that it can bind to both the enzyme and the enzyme-substrate complex. This suggests that LPA may not interact solely with the catalytic site. In this report we have prepared LPC analogs to help map out substrate structure-activity relationships. The structural variances include length and unsaturation of the fatty tail, choline and polar linker presence, acyl versus ether linkage of the hydrocarbon chain, and methylene and nitrogen replacement of the choline oxygen. All LPC analogs were assayed in competition with the synthetic substrate, FS-3, to show the preference ATX has for each alteration. Choline presence and methylene replacement of the choline oxygen were detrimental to ATX recognition. These findings provide insights into the structure of the enzyme in the vicinity of the catalytic site as well as suggesting that ATX produces rate enhancement, at least in part, by substrate destabilization. (C) 2009 Elsevier Ltd. All rights reserved.