1-[(2-formylcyclohexyl)disulfanyl]cyclohexanecarbaldehyde | 52958-74-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: 1-[(2-formylcyclohexyl)disulfanyl]cyclohexanecarbaldehyde
• 英文别名: 2,2'-dithiobis(cyclohexanecarbaldehyde)；1-[(Formylcyclohexyl)disulfanyl]cyclohexanecarbaldehyde；2,2'-dithiobis(cyclohexanecarboxaldehyde)；1-[(1-Formylcyclohexyl)disulfanyl]cyclohexane-1-carbaldehyde
• CAS: 52958-74-4
• 化学式: C₁₄H₂₂O₂S₂
• 分子量: 286.459
• InChiKey: MFXWPEWOLKKIHG-UHFFFAOYSA-N

物化性质

• 沸点：
  415.6±38.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(2-formylcyclohexyl)disulfanyl]cyclohexanecarbaldehyde 在 sodium tetrahydroborate 、 magnesium sulfate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 9.0h， 生成 5-[[1-[[1-[(5-Hydroxypentylamino)methyl]cyclohexyl]disulfanyl]cyclohexyl]methylamino]pentan-1-ol
  参考文献：
  名称：

  双氯芬酸的亚硝基硫醇酯：保留胃肠道的前药的合成和药理学表征。

  摘要：

  尽管其广泛使用，双氯芬酸仍具有非甾体抗炎药（NSAIDs）常见的胃肠道疾病，可通过同时服用胃肠道细胞保护剂（如一氧化氮（NO））来减轻。已合成了一系列含有亚硝基硫醇（-S-NO）部分作为NO供体官能团的新型双氯芬酸酯，并在体内对其生物利用度，药理活性和胃刺激性进行了评估。所有S-NO-双氯芬酸衍生物均作为口服生物可利用的前药，对小鼠口服后15分钟内在血浆中产生大量的双氯芬酸。在等摩尔口服剂量下，S-NO-双氯芬酸衍生物（20a-21b）在角叉菜胶诱发的爪水肿试验和小鼠苯基苯醌诱发的扭体试验中显示出与双氯芬酸相当的大鼠抗炎和镇痛活性。所有测试的S-NO-双氯芬酸衍生物（20a-21b）都是保胃的，与大鼠中等摩尔剂量的双氯芬酸引起的胃损害相比，它们引起的胃损害明显更少。双氯芬酸的亚硝基硫醇酯包含一类新的NO供体化合物，具有作为非甾体类抗炎药的治疗潜力，具有增强的胃安全性。所有测试的S-NO-双

  DOI：

  10.1021/jm000178w
• 作为产物：
  描述：

  环己烷基甲醛 在 二氯化二硫 作用下， 以70%的产率得到1-[(2-formylcyclohexyl)disulfanyl]cyclohexanecarbaldehyde
  参考文献：
  名称：

  Oxathiaphospholane方法合成P-手性，同位异构的脱氧（核糖核苷硫代磷酸酯）和用氧同位素标记的磷酸酯。

  摘要：

  非对映体纯和经同位素标记的5'-O-DMT-核苷-3'-O-（2-硫代和-氧代-4,4-“螺”-戊亚甲基-1,3,2- [ 18 O]氧代磷杂环戊烷）将其用于P-手性，同位素标记的寡核苷酸硫代磷酸酯和磷酸酯以及“嵌合” PS 18 O / P 18 O低聚物的立体控制合成，而不会损失同位素富集。DBU ＝ 1，8-二氮杂双环[5.4.0]十一碳-7-烯，DMT ＝ 4，4′-二甲氧基三苯甲基，ROH ＝ 3′-O-乙酰胸苷，Bz ＝苯甲酰基。

  DOI：

  10.1002/1521-3773(20010202)40:3<610::aid-anie610>3.0.co;2-w

文献信息

• Nitrosated and nitrosylated nonsteroidal antiinflammatory compounds, compositions and methods of use
  申请人：NitroMed, Inc.

  公开号：US06297260B1

  公开（公告）日：2001-10-02

  The present invention describes novel nitrosated and/or nitrosylated nonsteroidal antiinflammatory compounds, and novel compositions comprising at least one nitrosated and/or nitrosylated nonsteroidal antiinflammatory compound, and, optionally, at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase. The present invention also provides methods for treating, preventing and/or reducing inflammation, pain, and fever; decreasing or reversing the gastrointestinal, renal and other toxicities resulting from the use of nonsteroidal antiinflammatory drugs; treating and/or preventing gastrointestinal disorders; treating inflammatory disease states and disorders; and treating and/or preventing ophthalmic diseases or disorders.

  本发明描述了新颖的硝化和/或亚硝化非甾体抗炎化合物，以及包含至少一种硝化和/或亚硝化非甾体抗炎化合物的新型组合物，还可以包含至少一种捐赠、转移或释放一氧化氮、提高内源性内皮源性舒张因子水平、刺激内源性一氧化氮合成或是一氧化氮合酶底物的化合物。本发明还提供了治疗、预防和/或减轻炎症、疼痛和发热的方法；减少或逆转使用非甾体抗炎药物导致的胃肠道、肾脏和其他毒性反应；治疗和/或预防胃肠道疾病；治疗炎症性疾病状态和疾病；以及治疗和/或预防眼科疾病或疾病的方法。
• Exploration of Pyrrolobenzodiazepine (PBD)-Dimers Containing Disulfide-Based Prodrugs as Payloads for Antibody–Drug Conjugates
  作者：Zhonghua Pei、Chunjiao Chen、Jinhua Chen、Josefa dela Cruz-Chuh、Reginald Delarosa、Yuzhong Deng、Aimee Fourie-O’Donohue、Isabel Figueroa、Jun Guo、Weiwei Jin、S. Cyrus Khojasteh、Katherine R. Kozak、Brandon Latifi、James Lee、Guangmin Li、Eva Lin、Liling Liu、Jiawei Lu、Scott Martin、Carl Ng、Trung Nguyen、Rachana Ohri、Gail Lewis Phillips、Thomas H. Pillow、Rebecca K. Rowntree、Nicola J. Stagg、David Stokoe、Sheila Ulufatu、Vishal A. Verma、John Wai、Jing Wang、Keyang Xu、Zijin Xu、Hui Yao、Shang-Fan Yu、Donglu Zhang、Peter S. Dragovich

  DOI：10.1021/acs.molpharmaceut.8b00431

  日期：2018.9.4

  (PBD) monomers containing various disulfide-based prodrugs were evaluated for their ability to undergo activation (disulfide cleavage) in vitro in the presence of either glutathione (GSH) or cysteine (Cys). A good correlation was observed between in vitro GSH stability and in vitro cytotoxicity toward tumor cell lines. The prodrug-containing compounds were typically more potent against cells with relatively

  许多含有各种二硫化物系前药的细胞毒性pyrrolobenzodiazepine（PBD）的单体对它们进行活化（二硫化物断开）的能力进行了评价在体外在任一谷胱甘肽（GSH）或半胱氨酸（Cys）的存在。在体外GSH稳定性和体外对肿瘤细胞系的细胞毒性之间观察到良好的相关性。含前药的化合物通常对细胞内GSH含量较高的细胞（例如KPL-4细胞）更有效。随后，由PBD二聚体构建了几种抗体-药物结合物（ADC），这些结合物结合了选定的基于二硫键的前药。此类HER2偶联物在体外对KPL-4细胞表现出有效的抗增殖活性以抗原依赖性方式。然而，大多数这样的实体中所含的二硫键前药对来自各种物种的全血来说是不稳定的。含有巯基苯酚的二硫键前药的一种靶向HER2的偶联物是这种稳定性趋势的例外。它在KPL-4体内功效模型中显示出强效活性，其活性比相应的母体ADC所展示的活性弱约三倍。与不含前药的母体ADC相比，相同的含前
• First Examples of Oxidizing Aldehydes to Carboxylic Acids in the Presence of a Tertiary Disulfide Functional Group: Synthesis of Novel Diacid-disulfides
  作者：Xinqin Fang、Upul K. Bandarage、Tiansheng Wang、Joseph D. Schroeder、David S. Garvey

  DOI：10.1055/s-2003-37518

  日期：——

  The disulfide functionality exists in numerous organic compounds of interest in both chemistry and biology. In view of the fact that the disulfide function is highly susceptible to further oxidation by a broad range of agents, conducting a chemoselective oxidation without further oxidizing the disulfide group poses a synthetic challenge. Disclosed herein are the first examples of such an oxidation in which a series of aldehyde disulfides (1a-e) were converted to the corresponding symmetrical carboxylic acid disulfides (2a-e), utilizing sodium chlorite as the oxidant, and dimethyl sulf­oxide as both a reaction solvent and an efficient hypochlorous acid scavenger.

  二硫官能团存在于化学和生物学领域中许多令人感兴趣的有机化合物中。鉴于二硫功能极易被多种介质进一步氧化，在不进一步氧化二硫基团的情况下进行化学选择性氧化是一项合成挑战。本文公开了此类氧化的首个实例，利用亚氯酸钠作为氧化剂，二甲亚砜作为反应溶剂和有效的次氯酸清除剂，将一系列醛二硫化物（1a-e）转化为相应的对称羧酸二硫化物（2a-e）。
• Nitrosated and nitrosylated nonsteroidal antiinflammatory compounds, compositons and methods of use
  申请人：——

  公开号：US20020016322A1

  公开（公告）日：2002-02-07

  The present invention describes novel nitrosated and/or nitrosylated nonsteroidal antiinflammatory compounds, and novel compositions comprising at least one nitrosated and/or nitrosylated nonsteroidal antiinflammatory compound, and, optionally, at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase. The present invention also provides methods for treating, preventing and/or reducing inflammation, pain, and fever; decreasing or reversing the gastrointestinal, renal and other toxicities resulting from the use of nonsteroidal antiinflammatory drugs; treating and/or preventing gastrointestinal disorders; treating inflammatory disease states and disorders; and treating and/or preventing ophthalmic diseases or disorders.

  本发明描述了新型的亚硝酸化和/或亚硝基化的非甾体抗炎化合物，以及包含至少一种亚硝酸化和/或亚硝基化的非甾体抗炎化合物的新型组合物，以及可选地含有至少一种捐赠、转移或释放一氧化氮、提高内皮源性松弛因子内源水平、刺激内源性一氧化氮合成或是一氧化氮合酶底物的化合物。本发明还提供了治疗、预防和/或减轻炎症、疼痛和发热的方法；减少或逆转由非甾体抗炎药物使用引起的胃肠道、肾脏和其他毒性；治疗和/或预防胃肠道疾病；治疗炎症性疾病和疾病状态；以及治疗和/或预防眼科疾病或疾病状态。
• Deoxyribonucleoside 3‘-<i>O</i>-(2-Thio- and 2-Oxo-“spiro”-4,4-pentamethylene-1,3,2-oxathiaphospholane)s:  Monomers for Stereocontrolled Synthesis of Oligo(deoxyribonucleoside phosphorothioate)s and Chimeric PS/PO Oligonucleotides
  作者：Wojciech J. Stec、Bolesław Karwowski、Małgorzata Boczkowska、Piotr Guga、Maria Koziołkiewicz、Marek Sochacki、Michał W. Wieczorek、Jarosław Błaszczyk

  DOI：10.1021/ja973801j

  日期：1998.7.1

  New monomers, 5'-O-DMT-deoxyribonucleoside 3'-O-(2-thio-"spiro"-4,4-pentamethylene-1,3,2-oxathiaphospholane)s, were prepared and used for the stereocontrolled synthesis of PS-Oligos via the oxathiaphospholane approach. These monomers and their Zero analogues were used for the synthesis of "chimeric" constructs (PS/PO-Oligos) possessing phosphate and P-stereodefined phosphorothioate internucleotide linkages. The yield of a single coupling step is approximately 92-95%, and resulting oligomers are free of nucleobase- and sugar-phosphorothioate backbone modifications. Thermal dissociation studies showed that for heteroduplexes formed by [R-P]-, [S-P]-, or [mix]-PS/PO-T-10 with dA(12), dA(30), Or poly(dA), for each template, the melting temperatures, as well as free Gibbs' energies of dissociation process, are virtually equal. Stereochemical evidence derived from crystallographic analysis of one of the oxathiaphospholane monomers strongly supports the participation of pentacoordinate intermediates in the mechanism of the oxathiaphospholane ring-opening condensation.