2-mercaptoethylidene-1,1-bisphosphonic acid | 207606-36-8

• 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: 2-mercaptoethylidene-1,1-bisphosphonic acid
• 英文别名: 2-mercaptoethane-1,1-biphosphonic acid；HSEDP；2-mercaptoethane-1,1-diphosphonic acid；(1-Phosphono-2-sulfanylethyl)phosphonic acid
• CAS: 207606-36-8
• 化学式: C₂H₈O₆P₂S
• 分子量: 222.095
• InChiKey: XNYOUTARHBNRAE-UHFFFAOYSA-N

物化性质

• 沸点：
  566.7±60.0 °C(Predicted)
• 密度：
  1.943±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  11
• 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：
  116
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-mercaptoethylidene-1,1-bisphosphonic acid 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 2,2-diphosphonoethanesulphonic acid
  参考文献：
  名称：

  Bone-seeking complexes of technetium-99m

  摘要：

  用于制备骨扫描剂的一种组合物，包括式（I）的双膦酸混合物，其中R.sup.1和R.sup.3可以是相同或不同的基团，选自H，-SO.sub.3 H和可能含有一个或多个杂原子的低级脂肪基团，其中至少含有一个-SO.sub.3 H基团; R.sup.2是选自H，-OH，-NH.sub.2，-NHMe，-NMe.sub.2和低级烷基（可选地被一个或多个极性基团取代）的基团; R.sup.4是选自H，-OH，-NH.sub.2，-NHMe，-NMe.sub.2，-SO.sub.3 H和一个或多个极性基团取代的低级烷基的基团; n为0或1; 假设n为0时，R.sup.1不是H，当n为1时，R.sup.1和R.sup.3不能都是H; 或其无毒盐，以及还原剂对过碘酸根离子。将锝-99m作为过碘酸根离子的水溶液加入组合物中，形成Tc-99m和双膦酸盐的复合物。该复合物用作骨扫描剂，且迅速被骨吸收，产生高清晰度的扫描。

  公开号：

  US04810486A1
• 作为产物：
  描述：

  2-(S-isothiouronio)ethane-1,1-bisphosphonic acid betaine 在 甲胺 作用下， 以 水 为溶剂， 生成 2-mercaptoethylidene-1,1-bisphosphonic acid
  参考文献：
  名称：

  摘要：

  Purpose. This work was aimed at synthesizing novel bisphosphonates (BPs) and examining them in comparison to clinically used BPs such as pamidronate and alendronate, and to tetracycline, in order to evaluate their potential as anticalcification and antiresorption agents. The correlation between the various models was examined in order to establish facile experimental models for pre-screening of potential compounds.Methods. Nitrogen-containing heterocyclic, novel BPs such as 2-(3-methylimidazolio) ethylidene-1,1-bisphosphonic acid betaine (VS-5b), 2-(2-dimethylamino-4-pyrazinio)ethylidene-1,1-bisphosphonic acid betaine (VS-6b), and 2-(2-alpha-pyridylethylthio) ethylidene-1,1-bisphosphonic acid (ISA-225), were synthesized and evaluated in comparison to clinically used BPs, in various experimental models of resorption and calcification.Results. The physicochemical properties of the novel compounds are slightly different than the BPs in clinical use: the pKa values are lower, the affinity for hydroxyapatite is lower and the solubilities of the calcium salts are higher. The anticalcification potencies of the novel compounds were high and ranked as follows: alendronate = pamidronate > VS-6b = VS-5b = ISA-225 > tetracycline. The in vivo antiresorption activity of VS-5b and VS-6b in comparison to that of the clinically employed, pamidronate, was shown to be similar and higher, respectively.Conclusions. The anticalcification activity of the novel compounds as well as that of tetracycline was lower than that of alendronate. The antiresorption activity of VS-6b was similar to that of pamidronate. A good correlation between the different models was found, enabling the facile screening of novel compounds. The activities of tetracycline and EDTA highlight the distinct behavior of BPs as "crystal poison." In addition, tetracycline was found to be a potent anticalcification agent in the ectopic calcification model.

  DOI：

  10.1023/a:1011990129437

文献信息

• ——
  作者：Hagit Cohen、Vered Solomon、Ivan S. Alferiev、Eli Breuer、Asher Ornoy、Natan Patlas、Naomi Eidelman、Gerhard Hägele、Gershon Golomb

  DOI：10.1023/a:1011990129437

  日期：——

  Purpose. This work was aimed at synthesizing novel bisphosphonates (BPs) and examining them in comparison to clinically used BPs such as pamidronate and alendronate, and to tetracycline, in order to evaluate their potential as anticalcification and antiresorption agents. The correlation between the various models was examined in order to establish facile experimental models for pre-screening of potential compounds.Methods. Nitrogen-containing heterocyclic, novel BPs such as 2-(3-methylimidazolio) ethylidene-1,1-bisphosphonic acid betaine (VS-5b), 2-(2-dimethylamino-4-pyrazinio)ethylidene-1,1-bisphosphonic acid betaine (VS-6b), and 2-(2-alpha-pyridylethylthio) ethylidene-1,1-bisphosphonic acid (ISA-225), were synthesized and evaluated in comparison to clinically used BPs, in various experimental models of resorption and calcification.Results. The physicochemical properties of the novel compounds are slightly different than the BPs in clinical use: the pKa values are lower, the affinity for hydroxyapatite is lower and the solubilities of the calcium salts are higher. The anticalcification potencies of the novel compounds were high and ranked as follows: alendronate = pamidronate > VS-6b = VS-5b = ISA-225 > tetracycline. The in vivo antiresorption activity of VS-5b and VS-6b in comparison to that of the clinically employed, pamidronate, was shown to be similar and higher, respectively.Conclusions. The anticalcification activity of the novel compounds as well as that of tetracycline was lower than that of alendronate. The antiresorption activity of VS-6b was similar to that of pamidronate. A good correlation between the different models was found, enabling the facile screening of novel compounds. The activities of tetracycline and EDTA highlight the distinct behavior of BPs as "crystal poison." In addition, tetracycline was found to be a potent anticalcification agent in the ectopic calcification model.
• Bone-seeking complexes of technetium-99m
  申请人：Amersham International plc.

  公开号：US04810486A1

  公开（公告）日：1989-03-07

  A composition for use in the preparation of a bone-scanning agent comprises a mixture of a bis-phosphonic acid of formula (I), wherein R.sup.1 and R.sup.3 may be the same or different group selected from H, --SO.sub.3 H and a lower aliphatic group which may optionally contain one or more hetero atoms and which contains at least one --SO.sub.3 H group; R.sup.2 is a group selected from H, --OH, --NH.sub.2, --NHMe, --NMe.sub.2 and lower alkyl optionally substituted by one or more polar groups; R.sup.4 is a group selected from H, --OH, --NH.sub.2 --NHMe, --NMe.sub.2, --SO.sub.3 H and a lower alkyl optionally substituted by one or more polar groups; and n is 0 or 1; with the proviso that when n is 0, R.sup.1 is not H and that when n is 1, R.sup.1 and R.sup.3 cannot both be H; or a non-toxic salt thereof, together with a reducing agent for pertechnetate ions. Technetium-99m, as an aqueous solution of pertechnetate ions, is added to the composition to form a complex of Tc-99m, and the bisphosphonate. The complex is useful as a bone-scanning agent and is rapidly taken up in bone to give scans of high definition.

  用于制备骨扫描剂的一种组合物，包括式（I）的双膦酸混合物，其中R.sup.1和R.sup.3可以是相同或不同的基团，选自H，-SO.sub.3 H和可能含有一个或多个杂原子的低级脂肪基团，其中至少含有一个-SO.sub.3 H基团; R.sup.2是选自H，-OH，-NH.sub.2，-NHMe，-NMe.sub.2和低级烷基（可选地被一个或多个极性基团取代）的基团; R.sup.4是选自H，-OH，-NH.sub.2，-NHMe，-NMe.sub.2，-SO.sub.3 H和一个或多个极性基团取代的低级烷基的基团; n为0或1; 假设n为0时，R.sup.1不是H，当n为1时，R.sup.1和R.sup.3不能都是H; 或其无毒盐，以及还原剂对过碘酸根离子。将锝-99m作为过碘酸根离子的水溶液加入组合物中，形成Tc-99m和双膦酸盐的复合物。该复合物用作骨扫描剂，且迅速被骨吸收，产生高清晰度的扫描。