3-氨基磺酰基氧基丁烷-2-基氨基磺酸 | 77658-12-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 中文名称: 3-氨基磺酰基氧基丁烷-2-基氨基磺酸
• 英文名称: Sulfamic acid 1-methyl-2-sulfamoyloxy-propyl ester
• 英文别名: 2,3-Disulfamoyloxybutane；3-sulfamoyloxybutan-2-yl sulfamate
• CAS: 77658-12-9
• 化学式: C₄H₁₂N₂O₆S₂
• 分子量: 248.281
• InChiKey: GAGXXVRMSZDTMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2935009090

反应信息

• 作为产物：
  描述：

  2,3-丁二醇 在 氨基磺酰氯 、 sodium hydride 作用下， 生成 3-氨基磺酰基氧基丁烷-2-基氨基磺酸
  参考文献：
  名称：

  一系列N-未取代的氨基磺酸盐的男性合成和抗雄性评估。

  摘要：

  已经合成了一系列六种脂族和一个碳环N-未取代的氨基磺酸盐，并被评估为潜在的雄性抗生育剂。当对雄性大鼠口服给药时，脂族氨基磺酸盐中的三种，1,2-乙二氨基磺酸盐（1），1,3-丙二氨基磺酸盐（2）和1,4-丁二氨基磺酸盐（3）导致数量减少。怀孕的女性和/或植入，以及增加的胚胎和胎儿吸收。通过用氨磺酰氯处理适当的乙二醇盐或通过用三氟乙酸裂解氨基磺酸叔丁基酯来制备化合物。

  DOI：

  10.1021/jm00139a029

文献信息

• Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with bis-sulfamates
  作者：Jean-Yves Winum、Silvia Pastorekova、Lydia Jakubickova、Jean-Louis Montero、Andrea Scozzafava、Jaromir Pastorek、Daniela Vullo、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2004.11.058

  日期：2005.2

  A series of bis-sulfamates incorporating aliphatic, aromatic, or betulinyl moieties in their molecules was obtained by reaction of the corresponding diols/diphenols with sulfamoyl chloride. The library of bis-sulfamates thus obtained was tested for the inhibition of three physiologically relevant human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes, the cytosolic hCA I and II, and the transmembrane, tumor-associated hCA IX. The new compounds reported here inhibited hCA I with K-I s in the range of 79 nM-16.45 muM, hCA II with K-I s in the range of 6-643 nM, and hCA IX with K-I s in the range of 4-5400 nM. Several low nanomolar hCA IX inhibitors were detected, such as 1,8-octylene-bis-sulfamate or 1,10-decylene-bis-sulfamate (K-I s in the range of 4-7 nM), which showed good selectivity ratios (in the range of 3.50-3.85) for hCA IX over hCA II inhibition. The most selective hCA IX inhibitor was phenyl-1,4-dimethylene-bis-sulfamate (K-I of 61.6 nM), which was a 10.43 times better hCA IX than hCA II inhibitor. These derivatives are interesting candidates for the development of novel antitumor therapies targeting hypoxic tumors, since hCA IX is highly overexpressed in such tissues, and its presence is correlated with bad prognosis and unfavorable clinical outcome. (C) 2004 Elsevier Ltd. All rights reserved.
• HIRSCH A. F.; KASULANIS C.; KRAFT L.; MALLORY R. A.; POWELL G.; WONG B., J. MED. CHEM., 1981, 24, NO 7, 901-903
  作者：HIRSCH A. F.、 KASULANIS C.、 KRAFT L.、 MALLORY R. A.、 POWELL G.、 WONG B.

  DOI：——

  日期：——