1-hydroxy-1,12-dicarba-closo-dodecaborane | 54360-43-9

• 英文名称: 1-hydroxy-1,12-dicarba-closo-dodecaborane
• 英文别名: 1-hydroxy-1,12-dicarba-closo-dodecaborane(12)；1-hydroxy-para-carborane；1,12-C2B10H11-1-OH
• CAS: 54360-43-9
• 化学式: C₂H₁₂B₁₀O
• 分子量: 160.227
• InChiKey: CTBWMKZSODKLNG-UHFFFAOYSA-N

物化性质

• 熔点：
  148 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1-hydroxy-1,12-dicarba-closo-dodecaborane 、 sodium hydride 以 四氢呋喃 为溶剂， 生成 sodium 1-oxy-1,12-dicarba-closo-dodecaboranyl
  参考文献：
  名称：

  C-Hydroxydicarba-closo-dodecaboranes

  摘要：

  An improved synthesis and a full characterization of all three 12-vertex C-hydroxydicarba-closo-dodecaboranes 1-3 are reported. These inorganic analogues of phenols are highly acidic, but unlike phenols, they are transparent in the near-UV region and are stable to oxidation. The structure of their oxyanions 1a-3a poses an interesting issue of a close versus a bridged nido form. Also described is an introduction of a functionalized spacer in position 2 of 1 designed to permit incorporation into more complex organic structures.

  DOI：

  10.1021/ic970796b
• 作为产物：
  描述：

  sodium hydroxide 、 1,12-dicarba-closo-dodecaborane(12) 在 n-BuLi 、 trimethyl borate 、 H₂O₂ 作用下， 以 乙醚 、 正己烷 、 水 为溶剂， 以96%的产率得到1,12-dihydroxy-1,12-dicarba-closo-dodecaborane
  参考文献：
  名称：

  轻松高效地合成C-羟基卡巴龙和C，C'-二羟基卡巴龙。

  摘要：

  C-羟基化的碳硼烷，碳硼烷醇具有令人关注的特性，这是由于其碳氢化合物笼罩的电子缺陷性，因此其羟基质子呈高酸性。我们在这里描述了通过碳硼烷基锂和三甲基硼酸酯的反应，然后在乙酸的存在下用过氧化氢氧化，得到相应的邻-，间-通过一锅法选择性地以高收率选择性地选择对羟基苯甲酸酯，对羟基苯甲酸酯2和对羟基苯甲酮2以及邻，间羟基和对二羟基碳烷酮3。以特别好的收率（2b，85％； 2c，85％； 3b，95％； 3c，96％）获得2和3的间-和对-碳烷异构体。

  DOI：

  10.1021/ic062025q

文献信息

• BORON COMPOUNDS AS INHIBITORS OF LIPOXYGENASE AND THE LIPOXYGENASE PATHWAY, AND PREPARATION AND USE THEREOF
  申请人：UNIVERSITÄT LEIPZIG

  公开号：US20190055268A1

  公开（公告）日：2019-02-21

  The invention relates to chemical compound of the general structure [A-R 3 —X—R 4 ] where A=[R 1 -R 2 ] or [R 1 ] R 1 =aryl, heteroaryl R 2 =alkyl, aryl, heteroaryl, carbonyl, thiocarbonyl, alkyl ester, alkyl thioester R 3 =O, S, NH X=closo- or nido-boron cluster R 4 = where Z=OH, SH, NH 2 where R 5 is selected from H, alkyl, aryl, heteroaryl, alkyl ether, alkyl thioether, alkylamine and R 6 is selected from alkyl, aryl, heteroaryl, alkyl ether, alkyl thioether, alkylamine and where R 3 and R 4 are in meta or para positions to one another, to a process for preparation thereof and to the use thereof, especially in medicine, for example in the inhibition of lipoxygenase.

  该发明涉及一般结构为[A-R3—X—R4]的化合物，其中A=[R1-R2]或[R1]，R1=芳基，杂环芳基，R2=烷基，芳基，杂环芳基，酰基，硫代酰基，烷基酯，烷基硫酯，R3=O，S，NH，X=closo-或nido-硼簇，R4=其中Z=OH，SH，NH2，R5为H，烷基，芳基，杂环芳基，烷基醚，烷基硫醚，烷基胺，R6为烷基，芳基，杂环芳基，烷基醚，烷基硫醚，烷基胺，且R3和R4相对于彼此处于间位或对位位置，涉及其制备方法及用途，特别是在医学领域，例如在抑制脂氧合酶方面的用途。
• Synthesis and In Vitro Biological Evaluation of p-Carborane-Based Di-tert-butylphenol Analogs
  作者：Sebastian Braun、Sanja Jelača、Markus Laube、Sven George、Bettina Hofmann、Peter Lönnecke、Dieter Steinhilber、Jens Pietzsch、Sanja Mijatović、Danijela Maksimović-Ivanić、Evamarie Hey-Hawkins

  DOI：10.3390/molecules28114547

  日期：——

  p-carborane and further substitution of the p-position resulted in four carborane-based di-tert-butylphenol analogs that showed no or weak COX inhibition but high 5-LO inhibitory activities in vitro. Cell viability studies on five human cancer cell lines revealed that the p-carborane analogs R-830-Cb, S-2474-Cb, KME-4-Cb, and E-5110-Cb exhibited lower anticancer activity compared to the related di-tert-butylphenols

  靶向炎症介质和相关信号通路可能为癌症治疗提供合理的策略。在作为类花生酸生物合成关键酶的双重环加氧酶-2 (COX-2)/5-脂氧合酶 (5-LO) 抑制剂中加入代谢稳定、空间要求高和疏水的碳硼烷是一种很有前途的方法。二叔丁基苯酚衍生物 R-830​​、S-2474、KME-4 和 E-5110 是有效的双重 COX-2/5-LO 抑制剂。对碳硼烷的掺入和对位的进一步取代产生了四种基于碳硼烷的二叔丁基苯酚类似物，它们在体外没有显示出 COX 抑制作用或表现出较弱的 COX 抑制活性，但在体外具有高 5-LO 抑制活性。对五种人类癌细胞系的细胞活力研究表明，对碳硼烷类似物 R-830​​-Cb、S-2474-Cb、KME-4-Cb、与相关的二叔丁基苯酚相比，E-5110-Cb 表现出较低的抗癌活性。有趣的是，R-830​​-Cb 不影响原代细胞的活力，并且比其碳基 R-830​​ 对应物更有效地抑制
• Carborane‐Based Tebufelone Analogs and Their Biological Evaluation In Vitro
  作者：Sebastian Braun、Svetlana Paskaš、Markus Laube、Sven George、Bettina Hofmann、Peter Lönnecke、Dieter Steinhilber、Jens Pietzsch、Sanja Mijatović、Danijela Maksimović‐Ivanić、Evamarie Hey‐Hawkins

  DOI：10.1002/cmdc.202300206

  日期：2023.7.17

  The presence of inflammatory mediators in the tumor microenvironment, such as cytokines, growth factors or eicosanoids, indicate cancer‐related inflammatory processes. Targeting these inflammatory mediators and related signal pathways may offer a rational strategy for the treatment of cancer. This study focuses on the incorporation of metabolically stable, sterically demanding, and hydrophobic dicarba‐closo‐dodecaboranes (carboranes) into dual cyclooxygenase‐2 (COX‐2)/5‐lipoxygenase (5‐LO) inhibitors that are key enzymes in the biosynthesis of eicosanoids. The di‐tert‐butylphenol derivative tebufelone represents a selective dual COX‐2/5‐LO inhibitor. The incorporation of meta‐ or para‐carborane into the tebufelone scaffold resulted in eight carborane‐based tebufelone analogs that show no COX inhibition but 5‐LO inhibitory activity in vitro. Cell viability studies on HT29 colon adenocarcinoma cells revealed that the observed antiproliferative effect of the para‐carborane analogs of tebufelone is enhanced by structural modifications that include chain elongation in combination with introduction of a methylene spacer resulting in higher anticancer activity compared to tebufelone. Hence, this strategy proved to be a promising approach to design potent 5‐LO inhibitors with potential application as cytostatic agents.

  摘要 肿瘤微环境中存在细胞因子、生长因子或二十酸等炎症介质，表明存在与癌症相关的炎症过程。靶向这些炎症介质和相关信号通路可为癌症治疗提供合理的策略。本研究的重点是将代谢稳定、立体要求高且疏水性的二卡巴-氯索-十二硼烷（硼烷）掺入环氧合酶-2（COX-2）/5-脂氧合酶（5-LO）双重抑制剂中，而环氧合酶-2/5-脂氧合酶（5-LO）是类二十烷生物合成过程中的关键酶。二叔丁基苯酚衍生物特布非龙是一种选择性 COX-2/5-LO 双重抑制剂。将元硼烷或对位硼烷并入替布非龙支架后，产生了八种基于硼烷的替布非龙类似物，它们在体外不显示 COX 抑制作用，但具有 5-LO 抑制活性。在 HT29 结肠腺癌细胞上进行的细胞活力研究表明，对位硼烷的特布非龙类似物通过结构修饰（包括链延长和引入亚甲基间隔物）增强了所观察到的抗增殖作用，与特布非龙相比，这些类似物具有更高的抗癌活性。因此，这种策略被证明是设计强效 5-LO 抑制剂的一种有前途的方法，有望用作细胞抑制剂。