(1S,2s)-1,2-N,N-双[(甲烷磺酰基)氨基]-环己烷 | 220150-70-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: (1S,2s)-1,2-N,N-双[(甲烷磺酰基)氨基]-环己烷
• 英文名称: (S,S)-1,2-N,N'-bis(methylsulfonylamino)cyclohexane
• 英文别名: (S,S)-1,2-bis(methanesulfonylamino)cyclohexane；(1S,2S)-1,2-N,N'-Bis[(methane-sulfonyl)amino]-cyclohexane；N-[(1S,2S)-2-(methanesulfonamido)cyclohexyl]methanesulfonamide
• CAS: 220150-70-9
• 化学式: C₈H₁₈N₂O₄S₂
• 分子量: 270.374
• InChiKey: JUWLQVLCYRNWSV-YUMQZZPRSA-N

物化性质

• 熔点：
  156-158 °C
• 沸点：
  428.5±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2s)-1,2-N,N-双[(甲烷磺酰基)氨基]-环己烷 、 (S,S)-1,2-N,N'-bis(phenylsulfonylamino)cyclohexane 、 (S,S)-1,2-N,N'-bis(2-naphthylsulfonylamino)cyclohexane 、 (3S,4S)-1-苄基吡咯烷-3,4-二醇 在 三乙胺 、 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 生成 (S,S,S,S,S,S)-BnNC4H6(OP((MeSO2N)2C6H10))2 、 (S,S,S,S,S,S)-BnNC4H6(OP((PhSO2N)2C6H10))(OP((MeSO2N)2C6H10)) 、 (S,S,S,S,S,S)-BnNC4H6(OP(((2-Naph)SO2N)2C6H10))(OP((MeSO2N)2C6H10)) 、 (S,S,S,S,S,S)-BnNC4H6(OP((PhSO2N)2C6H10))(OP(((2-Naph)SO2N)2C6H10)) 、 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  基于质谱筛选和双重质量标记策略的组合配体开发

  摘要：

  手性配体的混合物由简单的前体制备，并通过使用 ESI-MS 和准对映体底物的同时筛选在不对称 Pd 催化的烯丙基化中进行评估。

  DOI：

  10.1021/ja0740317
• 作为产物：
  描述：

  (1S,2S)-(+)-1,2-环己二胺 、 甲基磺酰氯 在 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 以92%的产率得到(1S,2s)-1,2-N,N-双[(甲烷磺酰基)氨基]-环己烷
  参考文献：
  名称：

  Discovery of Chiral Cyclopropyl Dihydro-Alkylthio-Benzyl-Oxopyrimidine (S-DABO) Derivatives as Potent HIV-1 Reverse Transcriptase Inhibitors with High Activity Against Clinically Relevant Mutants

  摘要：

  The role played by stereochemistry in the C2-substituent (left part) on the S-DABO scaffold for anti-HIV-1 activity has been investigated for the first time. A series of S-DABO analogues, where the double bond in the C2-substituent is replaced by an enantiopure isosteric cyclopropyl moiety, has been synthesized, leading to the identification of a potent lead compound endowed with picomolar activity against RT (wt) and nanomolar activity against selected drug-resistant mutants. Molecular modeling calculation, enzymatic studies, and surface plasmon resonance experiments allowed us to rationalize the biological behavior of the synthesized compounds, which act as mixed-type inhibitors of HIV-1 RT K103N, with a preferential association to the enzyme-substrate complex. Taken together, our data show that the right combination of stereochemistry on the left and right parts (C6-substituent) of the S-DABO scaffold plays a key role in the inhibition of both wild-type and drug-resistant enzymes, especially the K103N mutant.

  DOI：

  10.1021/jm801330n
• 作为试剂：
  描述：

  二碘甲烷 、 p-methoxycinnamyl alcohol 在 (1S,2s)-1,2-N,N-双[(甲烷磺酰基)氨基]-环己烷 、 diethylzinc 、 zinc(II) iodide 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到(1S,2S)-2-(4-methoxyphenyl)cyclopropylmethanol
  参考文献：
  名称：

  Discovery of Chiral Cyclopropyl Dihydro-Alkylthio-Benzyl-Oxopyrimidine (S-DABO) Derivatives as Potent HIV-1 Reverse Transcriptase Inhibitors with High Activity Against Clinically Relevant Mutants

  摘要：

  The role played by stereochemistry in the C2-substituent (left part) on the S-DABO scaffold for anti-HIV-1 activity has been investigated for the first time. A series of S-DABO analogues, where the double bond in the C2-substituent is replaced by an enantiopure isosteric cyclopropyl moiety, has been synthesized, leading to the identification of a potent lead compound endowed with picomolar activity against RT (wt) and nanomolar activity against selected drug-resistant mutants. Molecular modeling calculation, enzymatic studies, and surface plasmon resonance experiments allowed us to rationalize the biological behavior of the synthesized compounds, which act as mixed-type inhibitors of HIV-1 RT K103N, with a preferential association to the enzyme-substrate complex. Taken together, our data show that the right combination of stereochemistry on the left and right parts (C6-substituent) of the S-DABO scaffold plays a key role in the inhibition of both wild-type and drug-resistant enzymes, especially the K103N mutant.

  DOI：

  10.1021/jm801330n

文献信息

• COMPOUNDS AND SYNTHETIC METHODS FOR THE PREPARATION OF RETINOID X RECEPTOR-SPECIFIC RETINOIDS
  申请人：Io Therapeutics, Inc.

  公开号：US20190152888A1

  公开（公告）日：2019-05-23

  Provided herein are compounds useful for the preparation of compounds that have retinoid-like biological activity. Also provided herein are processes for the preparation of compounds that have retinoid-like biological activity.

  本文提供了用于制备具有类视黄醇生物活性化合物的化合物。本文还提供了制备具有类视黄醇生物活性化合物的过程。
• Compounds and synthetic methods for the preparation of retinoid X receptor-specific retinoids
  申请人：Io Therapeutics, Inc.

  公开号：US10590059B2

  公开（公告）日：2020-03-17

  Provided herein are compounds useful for the preparation of compounds that have retinoid-like biological activity. Also provided herein are processes for the preparation of compounds that have retinoid-like biological activity.

  本文提供的化合物可用于制备具有类视黄醇生物活性的化合物。本文还提供了制备具有类视黄醇生物活性的化合物的工艺。
• AMIDOPROPOXYPHENYL OREXIN RECEPTOR ANTAGONISTS
  申请人：Merck & Co., Inc.

  公开号：EP1871752A1

  公开（公告）日：2008-01-02
• [EN] AMIDOPROPOXYPHENYL OREXIN RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RÉCEPTEUR DE L'OREXINE DE TYPE AMIDOPROPOXYPHÉNYLE
  申请人：MERCK & CO INC

  公开号：WO2006110626A1

  公开（公告）日：2006-10-19

  [EN] The present invention is directed to amidopropoxyphenyl compounds which are antagonists of orexin receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which orexin receptors are involved.
  [FR] La présente invention a pour objet des composés de type amidopropoxyphényle qui sont des antagonistes des récepteurs de l'orexine, et qui peuvent être employés dans le traitement prophylactique ou thérapeutique de troubles neurologiques et psychiatriques et de maladies dans lesquelles interviennent les récepteurs de l'orexine. La présente invention concerne également des préparations pharmaceutiques comprenant lesdits composés, ainsi que l'emploi desdits composés et préparations dans le traitement prophylactique ou thérapeutique de maladies dans lesquelles interviennent les récepteurs de l'orexine.
• Combinatorial Ligand Development Based on Mass Spectrometric Screening and a Double Mass-Labeling Strategy
  作者：Christian Markert、Pirmin Rösel、Andreas Pfaltz

  DOI：10.1021/ja0740317

  日期：2008.3.1

  Mixtures of chiral ligands were prepared from simple precursors and evaluated in the asymmetric Pd-catalyzed allylation by simultaneous screening using ESI-MS and quasienantiomeric substrates.

  手性配体的混合物由简单的前体制备，并通过使用 ESI-MS 和准对映体底物的同时筛选在不对称 Pd 催化的烯丙基化中进行评估。