estra-1,3,5(10)-trien-17-one-[3,2,e]-1',2',3'-oxathiazine-2',2'-dioxide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: estra-1,3,5(10)-trien-17-one-[3,2,e]-1',2',3'-oxathiazine-2',2'-dioxide
• 英文别名: (2S,5S,9S,10R)-5-methyl-17,17-dioxo-16-oxa-17lambda6-thia-18-azapentacyclo[11.8.0.02,10.05,9.015,20]henicosa-1(21),13,15(20),18-tetraen-6-one；(2S,5S,9S,10R)-5-methyl-17,17-dioxo-16-oxa-17λ6-thia-18-azapentacyclo[11.8.0.02,10.05,9.015,20]henicosa-1(21),13,15(20),18-tetraen-6-one
• 化学式: C₁₉H₂₁NO₄S
• 分子量: 359.446
• InChiKey: XDIFESNMZIAQHM-MVWRLGRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  estra-1,3,5(10)-trien-17-one-[3,2,e]-1',2',3'-oxathiazine-2',2'-dioxide 、 环己甲酸 在 dipotassium peroxodisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以87%的产率得到(3aS,3bR,11bS,13aS)-10-cyclohexyl-13a-methyl-2,3,3a,3b,4,5,11b,12,13,13a-decahydro-1H-cyclopenta[7,8]phenanthro[3,2-e][1,2,3]oxathiazin-1-one 8,8-dioxide
  参考文献：
  名称：

  银与脂肪族羧酸催化的环亚胺的脱羧C–H官能化

  摘要：

  在温和的反应条件下，已经实现了银催化的环状亚胺与丰富的脂肪族羧酸的C–H烷基化反应，生成相应的产物，收率中等至良好（32％–91％）。此外，还进行了克级反应，药物的后期修饰，产物的合成转化以及催化策略的进一步应用。初步研究表明该反应经历了自由基过程。

  DOI：

  10.1016/j.cclet.2021.03.011
• 作为产物：
  描述：

  2-formyl-estrone 在 sodium hydride 、 甲酸 、 氯磺酰异氰酸酯 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 5.0h， 以52%的产率得到estra-1,3,5(10)-trien-17-one-[3,2,e]-1',2',3'-oxathiazine-2',2'-dioxide
  参考文献：
  名称：

  Steroidal oxathiazine inhibitors of estrone sulfatase

  摘要：

  The presence of estrone sulfatase in breast tumors and the high levels of circulating estrone sulfate may contribute the major portion of estrogen synthesized locally in breast tissues through conversion of estrone sulfate to estrone by the enzyme. Using inhibitors of estrone sulfatase for the treatment of estrogen-dependent (estrogen receptor positive, ER+) breast cancer could be a very effective therapeutic strategy for the treatment of estrogen-dependent breast tumors in postmenopausal women. Therefore, we designed and synthesized several steroidal 2',3-oxathiazines that inhibit estrone sulfatase and have greatly reduced estrogenic side effects. Our in vitro studies indicate that the oxathiazine compounds have inhibitory activity on estrone sulfatase in MCF-7 human breast cancer cells. These estrone sulfatase inhibitors (ESIs) also inhibit the growth of MCF-7 cells induced by estrone sulfate. In addition, our in vivo experiments demonstrate that our ESIs have moderate antitumor activity against MCF-7 breast cancer xenografts in Balb/c athymic nude mice. The synthesis and biological activity of a number of these unique steroidal ESIs are described. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00118-6

文献信息

• Electrochemically driven oxidative C–H/N–H cross-coupling reactions of cyclic sulfamidate imines with primary anilines and secondary amines
  作者：Hai-Xia Wang、Zhi-Hao Li、Wan-Wan Li、Gui-Rong Qu、Qi-Liang Yang、Hai-Ming Guo

  DOI：10.1039/d2gc03218j

  日期：——

  oxidative C–H/N–H cross-coupling amination of cyclic sulfamidate imines under undivided electrolytic conditions via an atom- and step-economic method. In this transformation, a wide variety of cyclic or acyclic dialkyl amines, amino acid derivatives, and more challenging primary anilines acted as suitable substrates with good reaction outcomes. The synthetic advantage of this electrochemical method

  开发了一种电合成方法，用于在不分电解条件下通过氧化 C-H/N-H 交叉偶联胺化环状氨基磺酸酯原子和步骤经济方法。在这种转化中，多种环状或非环状二烷基胺、氨基酸衍生物和更具挑战性的伯苯胺作为合适的底物，具有良好的反应结果。这种电化学方法的综合优势通过高官能团兼容性（86 个例子）、易于放大至克级以及完成复杂生物相关分子的后期功能化而增强，这提供了一种具有广泛潜在应用的有效工具药物和合成化学的前景。机理研究表明，这种转变可能是通过一个激进的过程发生的。
• Silver-catalyzed decarboxylative C–H functionalization of cyclic aldimines with aliphatic carboxylic acids
  作者：Jingjing Wang、Xue Liu、Ziyan Wu、Feng Li、Tingting Qin、Siyuan Zhang、Weiguang Kong、Lantao Liu

  DOI：10.1016/j.cclet.2021.03.011

  日期：2021.9

  Silver-catalyzed decarboxylative C–H alkylation of cyclic aldimines with abundant aliphatic carboxylic acids has been realized under mild reaction conditions generating the corresponding products in moderate to good yields (32%–91%). In addition, a gram-scale reaction, late-stage modification of drug, synthetic transformation of the product, and further application of the catalytic strategy were also

  在温和的反应条件下，已经实现了银催化的环状亚胺与丰富的脂肪族羧酸的C–H烷基化反应，生成相应的产物，收率中等至良好（32％–91％）。此外，还进行了克级反应，药物的后期修饰，产物的合成转化以及催化策略的进一步应用。初步研究表明该反应经历了自由基过程。
• Steroidal oxathiazine inhibitors of estrone sulfatase
  作者：Richard H Peters、Wan-Ru Chao、Barbara Sato、Kazuhiko Shigeno、Nurulain T Zaveri、Masato Tanabe

  DOI：10.1016/s0039-128x(02)00118-6

  日期：2003.1

  The presence of estrone sulfatase in breast tumors and the high levels of circulating estrone sulfate may contribute the major portion of estrogen synthesized locally in breast tissues through conversion of estrone sulfate to estrone by the enzyme. Using inhibitors of estrone sulfatase for the treatment of estrogen-dependent (estrogen receptor positive, ER+) breast cancer could be a very effective therapeutic strategy for the treatment of estrogen-dependent breast tumors in postmenopausal women. Therefore, we designed and synthesized several steroidal 2',3-oxathiazines that inhibit estrone sulfatase and have greatly reduced estrogenic side effects. Our in vitro studies indicate that the oxathiazine compounds have inhibitory activity on estrone sulfatase in MCF-7 human breast cancer cells. These estrone sulfatase inhibitors (ESIs) also inhibit the growth of MCF-7 cells induced by estrone sulfate. In addition, our in vivo experiments demonstrate that our ESIs have moderate antitumor activity against MCF-7 breast cancer xenografts in Balb/c athymic nude mice. The synthesis and biological activity of a number of these unique steroidal ESIs are described. (C) 2002 Elsevier Science Inc. All rights reserved.