morpholino-(1S,4R)-10-camphorsulfonamide | 1239861-63-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: morpholino-(1S,4R)-10-camphorsulfonamide
• 英文别名: 7,7-dimethyl-1-(morpholinosulfonylmethyl)bicyclo[2.2.1]heptan-2-one；Camphersulfonsaeure-(10)-morpholid；4-(2-oxo-bornane-10-sulfonyl)-morpholine；7,7-dimethyl-1-(morpholine-4-sulfonylmethyl)-bicyclo[2.2.1]heptan-2-one；(1S,4R)-7,7-dimethyl-1-(morpholin-4-ylsulfonylmethyl)bicyclo[2.2.1]heptan-2-one
• CAS: 1239861-63-2
• 化学式: C₁₄H₂₃NO₄S
• 分子量: 301.407
• InChiKey: UFVYTBAYGAJUQD-BXUZGUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  morpholino-(1S,4R)-10-camphorsulfonamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以62 %的产率得到(1s,2r,4r)-7,7-Dimethyl-1-[(morpholinosulfonyl)methyl]bicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  (1S)-(+)-樟脑-10-磺酰胺类药物的合成及其抗丝状病毒活性评价

  摘要：

  合成了一系列在氮原子上含有各种取代基的新型(1S)-(+)-樟脑-10-磺酰胺，并使用基于水泡性口炎病毒的假病毒系统评估了它们对埃博拉病毒的抗病毒特性。C(2)原子上的羰基的还原导致抗病毒功效显着提高，而转化为肟则导致抗病毒活性几乎完全消失。根据对天然埃博拉病毒的抗病毒活性评价，先导化合物表现出中等的抑制活性。通过分子模型研究了先导化合物与埃博拉病毒糖蛋白结合位点的相互作用。对由于合成的配体和已知抑制剂与埃博拉病毒表面糖蛋白可能相互作用而引起的变化进行了比较分析。

  DOI：

  10.1007/s11172-023-4056-y
• 作为产物：
  描述：

  D(+)-10-樟脑磺酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 morpholino-(1S,4R)-10-camphorsulfonamide
  参考文献：
  名称：

  Synthesis of (1S)-(+)-camphor-10-sulfonic acid derivatives and investigations in vitro and in silico of their antiviral activity as the inhibitors of fi lovirus infections

  摘要：

  含有N-杂环的(1S)-(+)-樟脑-10-磺酰胺衍生物被合成。它们对埃博拉病毒和马尔堡病毒的抗病毒活性是利用基于水泡性口炎病毒的假病毒系统进行评估的。含有吗啉和三唑基团的衍生物显示出对埃博拉病毒糖蛋白最强的抑制活性。含有哌啶基团的化合物对马尔堡病毒表现出中等活性。还进行了合成的衍生物与埃博拉病毒糖蛋白结合位点的分子模型模拟。

  DOI：

  10.1007/s11172-019-2517-0

文献信息

• METHOD FOR PREPARING 2-MORPHOLINOISOBORNANE- 10-THIOL AND INTERMEDIATES FORMED THEREIN
  申请人：UANG Biin-Jiun

  公开号：US20110269955A1

  公开（公告）日：2011-11-03

  A method for preparing 2-morpholinoisobornane-10-thiol is disclosed, which has simplified steps and avoids the use of Na metal. Accordingly, it is advantageous to apply the method in a mass production.

  公开了一种制备2-吗啉异冰片烷-10-硫醇的方法，该方法步骤简化，避免使用钠金属。因此，在大规模生产中应用该方法具有优势。
• [EN] A PROCESS FOR THE MANUFACTURE OF CHIRAL CATALYSTS AND THEIR SALTS<br/>[FR] PROCÉDÉ POUR LA FABRICATION DE CATALYSEURS CHIRAUX ET DE LEURS SELS
  申请人：SCINOPHARM TAIWAN LTD

  公开号：WO2013080049A3

  公开（公告）日：2013-08-08
• Synthesis, structure and activity of sulfonamides derived from (+)-camphor in the enantioselective addition of diethylzinc to benzaldehyde
  作者：Anna Kozakiewicz、Małgorzata Ullrich、Mirosław Wełniak、Andrzej Wojtczak

  DOI：10.1016/j.molcata.2010.04.019

  日期：2010.7

  New chiral sulfonamides derived from (+)-camphor, with different substituents on camphor C2 and sulfonamide N, were synthesized. Their activity was tested in the reaction of Et2Zn addition to benzaldehyde. The yield of the reaction was 44-96%, the enantiomeric excess was 1-69%. Sulfonamides possessing the 2-hydroxyl group gave an excess of 1-(S)-phenylpropanol, while catalysts containing other sulfonamides gave 1-(R)-phenylpropanol as a major product. The best catalytic efficacy was observed for sulfonamides with (R)-C2-OH group, while the use of thioketo- and mercaptosulfonamides resulted in low enantiomeric excess and yields not exceeding 60%. Crystal structures have been determined for sulfonamides with N-benzyl moiety and different substituents on the C2 atom. The structural analysis revealed the presence of intramolecular N center dot center dot center dot O(C2) and O-sulfo center dot center dot center dot O(C2)H-bonds, what confirms the ability of these molecules to adopt the conformation required for their bidentate coordination to Ti(IV) via the sulfonamide group and substituent at C2. The coordination mode for investigated sulfonamides was determined with the IR spectra for five obtained Ti(IV) complexes and crystal structure analysis of the ligands. The 3D structures of Ti(IV) complex catalysts containing investigated sulfonamides were postulated, which are consistent with the reported chirality of the addition product and observed % ee. (C) 2010 Elsevier B.V. All rights reserved.
• Winicki,B. et al., Bulletin de la Societe Chimique de France, 1960, p. 1647 - 1648
  作者：Winicki,B. et al.

  DOI：——

  日期：——
• Synthesis of (1S)-(+)-camphor-10-sulfonic acid derivatives and investigations in vitro and in silico of their antiviral activity as the inhibitors of fi lovirus infections
  作者：A. S. Sokolova、D. V. Baranova、O. I. Yarovaya、D. S. Baev、O. A. Polezhaeva、A. V. Zybkina、D. N. Shcherbakov、T. G. Tolstikova、N. F. Salakhutdinov

  DOI：10.1007/s11172-019-2517-0

  日期：2019.5

  N-Heterocycle-containing (1S)-(+)-camphor-10-sulfonamide derivatives were synthesized. Their antiviral activity against the Ebola and Marburg viruses was estimated using a pseudovirus system based on the vesicular stomatitis virus. The derivatives bearing morpholine and triazole moieties demonstrated the highest inhibitory activity towards the Ebola virus glycoprotein. A moderate activity against the Marburg virus was found for a compound containing the piperidine moiety. A molecular modeling of the interaction between the synthesized derivatives and the binding site of glycoprotein of the Ebola virus was performed.

  含有N-杂环的(1S)-(+)-樟脑-10-磺酰胺衍生物被合成。它们对埃博拉病毒和马尔堡病毒的抗病毒活性是利用基于水泡性口炎病毒的假病毒系统进行评估的。含有吗啉和三唑基团的衍生物显示出对埃博拉病毒糖蛋白最强的抑制活性。含有哌啶基团的化合物对马尔堡病毒表现出中等活性。还进行了合成的衍生物与埃博拉病毒糖蛋白结合位点的分子模型模拟。