3-(1',2'-dicarbo-closo-dodecaborane-1'-yl)propanoic acid | 20693-22-5

• 英文名称: 3-(1',2'-dicarbo-closo-dodecaborane-1'-yl)propanoic acid
• 英文别名: 3-(1,2-dicarba-closo-dodecaboran-1-yl)propionic acid；1-CH2CH2COOH-1,2-C2B10H11
• CAS: 20693-22-5
• 化学式: C₅H₁₆B₁₀O₂
• 分子量: 216.291
• InChiKey: GCLOWAQCGCUVAO-UHFFFAOYSA-N

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：

  3-(1',2'-dicarbo-closo-dodecaborane-1'-yl)propanoic acid 、 4-[(6-aminohexyl)amino]-3-nitro-N-[2-(N-pyrrolidinyl)ethyl]-1,8-naphthalimide 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以47 %的产率得到4-[(6-[3–(1,2-dicarba-closo-dodecaborane-1-yl)propanamido]hexyl)amino]-3-nitro-N-[2-(N-pyrrolidinyl)ethyl]-1,8-naphthalimide
  参考文献：
  名称：

  碳硼烷基-1,8-萘酰亚胺嵌入剂诱导癌细胞系中溶酶体膜透化和铁焦亡

  摘要：

   抽象的 进行了碳硼烷-1,8-萘二甲酰亚胺缀合物的合成并评估了其DNA结合能力和抗癌活性。通过酰胺化和还原胺化反应合成了一系列 4-碳硼基-3-硝基-1,8-萘二甲酰亚胺衍生物、mitonafide 和 pinafide 类似物，并利用圆二色性研究了它们的小牛胸腺 DNA (ct-DNA) 结合特性、紫外可见光谱和热变性。结果显示，缀合物34 – 37与 ct-DNA 相互作用非常强烈（Δ T m = 10.00–13.00 °C），表明它们具有插入 DNA 的能力，但不会抑制拓扑异构酶 II 的活性。该缀合物在体外抑制了 HepG2 癌细胞系的细胞生长。相同的化合物导致 G2M 期停滞。与对照相比，用这些缀合物处理的细胞系显示出活性氧、谷胱甘肽和Fe 2+水平、脂质过氧化和线粒体膜电位的增加，表明铁死亡的参与。此外，这些缀合物在 HepG2 细胞中引起溶酶体膜通透，但在 MRC-5 细胞中则不然。

  DOI：

  10.1080/14756366.2023.2171028
• 作为产物：
  描述：

  trichloroethyl 3-(1',2'-dicarbo-closo-dodecaborane-1'-yl)propanoate 在 溶剂黄146 、 锌 作用下， 以 溶剂黄146 为溶剂， 以90%的产率得到3-(1',2'-dicarbo-closo-dodecaborane-1'-yl)propanoic acid
  参考文献：
  名称：

  Polyester-Based Carborane-Containing Dendrons

  摘要：

  New carborane-containing dendrons based on a 2,2-bis(hydroxymethyl) propanoic acid scaffold have been prepared for applications in boron neutron capture therapy. A generation-2 carborane-containing dendron carrying 40 boron atoms was the highest generation synthetically available due to the steric crowding. The structure of this dendron has been simulated by molecular dynamics. A 10-carbon linker carrying a carboxylic group has been installed at the focal point of the dendron to distance the attachment point from the sterically hindered core.

  DOI：

  10.1021/ic060866r

文献信息

• Microwave-Assisted Synthesis of 3,1,2- and 2,1,8-Re(I) and ^99mTc(I)−Metallocarborane Complexes
  作者：Andrew E. C. Green、Patrick W. Causey、Anika S. Louie、Andrea F. Armstrong、Laura E. Harrington、John F. Valliant

  DOI：10.1021/ic0605928

  日期：2006.7.1

  heating was used to prepare eta5-rhenium carborane complexes in aqueous reaction media. For carboranes bearing sterically demanding substituents, isomerization of the cage from 3,1,2 to 2,1,8 derivatives occurred concomitantly with complexation. Microwave heating was equally effective at the tracer level using technetium-99m, affording access to a new class of synthons for designing novel molecular

  微波加热用于在水性反应介质中制备η5-r碳硼烷配合物。对于带有空间上需要的取代基的碳硼烷，笼型从3,1,2到2,1,8衍生物的异构化伴随络合发生。使用tech 99m，微波加热在示踪剂水平上同样有效，为设计新型分子显像剂提供了新型合成子。
• Synthesis of boron cluster analogs of penicillin and their antibacterial activity
  作者：Daria Różycka、Zbigniew J. Leśnikowski、Agnieszka B. Olejniczak

  DOI：10.1016/j.jorganchem.2018.11.037

  日期：2019.2

  pharmacologically active molecules. A series of novel penicillin G analogs bearing lipophilic 1,2-dicarba-closo-dodecaborane (ortho-carborane), 1,7-dicarba-closo-dodecaborane (meta-carborane), or 1,12-dicarba-closo-dodecaborane (para-carborane) boron clusters, instead of the phenyl ring, were synthesized. The boron-cluster penicillin G analogs were obtained via amidation of 6-aminopenicillanic acid (6-APA)

  抗菌素耐药性（AMR）是人类健康面临的一项日益严峻的挑战。迫切需要开发可开发为临床有用药物的新型潜在客户。改变已成为医学基石的旧种类抗生素的想法已大为革新，以寻找克服抗生素耐药菌的方法。一个非常有趣的发展是在药理活性分子的设计中碳硼烷的实现。一系列新颖青霉素G的类似物的亲脂性轴承1,2- dicarba-闭合碳-dodecaborane（邻-carborane），1,7- dicarba-闭合碳-dodecaborane（元-carborane），或1,12- dicarba-闭合碳-dodecaborane（帕拉（-碳硼烷）硼簇，而不是苯环，被合成。经由的6-氨基青霉烷酸（6-APA）的酰胺化与获得的硼簇青霉素G类似物Ñ含有琥珀酰亚胺活性酯邻位，间位-或对位-carborane或者，含有类似物邻或对位合成-carborane使用邻-或对-碳硼烷簇酰氯。如此获得的化合物在体外针对革兰氏阳性
• Design, Synthesis, and Evaluation of Novel 3-Carboranyl-1,8-Naphthalimide Derivatives as Potential Anticancer Agents
  作者：Sebastian Rykowski、Dorota Gurda-Woźna、Marta Orlicka-Płocka、Agnieszka Fedoruk-Wyszomirska、Małgorzata Giel-Pietraszuk、Eliza Wyszko、Aleksandra Kowalczyk、Paweł Stączek、Andrzej Bak、Agnieszka Kiliszek、Wojciech Rypniewski、Agnieszka B. Olejniczak

  DOI：10.3390/ijms22052772

  日期：——

  We synthesized a series of novel 3-carboranyl-1,8-naphthalimide derivatives, mitonafide and pinafide analogs, using click chemistry, reductive amination and amidation reactions and investigated their in vitro effects on cytotoxicity, cell death, cell cycle, and the production of reactive oxygen species in a HepG2 cancer cell line. The analyses showed that modified naphthalic anhydrides and naphthalimides

  我们利用点击化学，还原胺化和酰胺化反应合成了一系列新颖的3-carbananyl-1,8-naphthalimide衍生物，mitonafide和pinafide类似物，并研究了它们在体外对细胞毒性，细胞死亡，细胞周期以及细胞生成的影响。 HepG2癌细胞系中的活性氧。分析表明，带有邻-或间-碳烷的改性萘酐和萘二甲酰亚胺表现出多种活性。萘二甲酰亚胺比萘二甲酸酐更具细胞毒性，对化合物9测得的最高IC 50值（3.10 µM）。这些化合物能够在G0 / G1或G2M期诱导细胞周期停滞，并促进细胞凋亡，自噬或肥大病。最有前途的缀合物35引起强烈的细胞凋亡并诱导ROS产生，这已通过DNA中2'-deoxy-8-oxoguanOSine的水平升高而得到证明。发现测试的结合物是弱拓扑异构酶II抑制剂和经典的DNA嵌入剂。化合物33，34，和36荧光染色的HepG2细胞中的溶酶体。此外，我们使用主成分分
• Acridine/Acridone–Carborane Conjugates as Strong DNA‐Binding Agents with Anticancer Potential
  作者：Daria Różycka、Aleksandra Kowalczyk、Marta Denel‐Bobrowska、Olga Kuźmycz、Magdalena Gapińska、Paweł Stączek、Agnieszka B. Olejniczak

  DOI：10.1002/cmdc.202200666

  日期：——

  Increasing ROS: A series of novel acridine/acridone-carborane conjugates were synthesised and investigated. Conjugate 30, containing meta-carborane, revealed dual activity as the most potent ct-DNA intercalator (with preservation of B-form DNA) and as a toxic agent against the HeLa cell line. This cytotoxicity is a result of increased intracellular reactive oxygen species (ROS) formation, higher than

  增加 ROS：合成并研究了一系列新型吖啶/吖啶酮-碳硼烷偶联物。含有间位碳硼烷的缀合物30显示出双重活性，作为最有效的 ct-DNA 嵌入剂（保留 B 型 DNA）和作为针对 HeLa 细胞系的毒剂。这种细胞毒性是细胞内活性氧 (ROS) 形成增加的结果，高于安吖啶诱导的 ROS 水平。
• Synthesis of <i>Ortho</i>- and <i>Meta</i>-Re(I)-Metallocarboranes in Water
  作者：Oyebola O. Sogbein、Andrew E. C. Green、Paul Schaffer、Raymond Chankalal、Edwin Lee、Brian D. Healy、Pierre Morel、John F. Valliant

  DOI：10.1021/ic0511221

  日期：2005.12.1

  A series of metallocarboranes of the types rac[M(CO)(3)(n(5)-7-R-7,8-C2B9H11)](-)and rac-[M(CO)(3)(n(5)-7-R-8-R'-7,8-C2B9H11)](-), and rac-[M(CO)(3)(n(5)-7-R-7,9-C2B9H11)](-) (M = Re) were prepared by reacting [NEt4](2)[Re(CO)(3)Br-3] or [Re(CO)(3-)(OH2)(3)]Br with the corresponding carboranes in the presence of aqueous solutions of either alkali metal or tetraalkylammonium fluoride salts. Carborane derivatives that were investigated included those containing pyridine, amino, carboxylic acid, carbohydrate, and aryl substituents, During the course of the research, it was discovered that Re metallocarboranes can be prepared directly from the respective closo-clusters under similar reaction conditions used with nido-carboranes. Reaction yields ranged from modest to excellent depending on the carborane isomer and the nature of the cage substituent(s). A crystal structure of an amine-substituted Re metal locarborane was obtained where the complex crystallized in the orthorhombic space group P2(1)2(1)2(1) with a = 8.982(2) angstrom, b 11.563(3) angstrom, c = 16.811(4) angstrom, (alpha = beta = gamma = 90 degrees, V = 1746.1(7) angstrom(3), Z = 4, and R1 = 0.0684.