(±)-(2-nitrophenyl)cyclohexylmethanol | 1621071-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (±)-(2-nitrophenyl)cyclohexylmethanol
• 英文别名: α-cyclohexyl-2-nitrobenzyl alcohol；cyclohexyl(2-nitrophenyl)methanol；(RS)-(2-nitropheny)-cyclohexylmethanol；(RS)-(2-nitropheny)cyclohexylmethanol；(+/-)-(2-Nitrophenyl)-cyclohexylmethanol；cyclohexyl-(2-nitrophenyl)methanol
• CAS: 1621071-03-1
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: ZFQMYWITOFQYGC-UHFFFAOYSA-N

物化性质

• 沸点：
  401.4±20.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N³-tert-butyloxycarbonyl-5-bromomethyl-3',5'-bis-O-tert-butyldimethylsilyl-2'-deoxyuridine 、 (±)-(2-nitrophenyl)cyclohexylmethanol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以25%的产率得到5-[1-((2-nitrophenyl)-1-(cyclohexyl)methoxy)methyl]-2'-deoxyuridine
  参考文献：
  名称：

  [EN] NOVEL NANOCARRIER DELIVERED CANCER CHEMOTHERAPEUTIC AGENTS
  [FR] NOUVEAUX AGENTS CHIMIOTHÉRAPEUTIQUES ANTICANCÉREUX DÉLIVRÉS PAR NANO-PORTEUR

  摘要：

  公开号：

  WO2014194250A3
• 作为产物：
  描述：

  2-硝基碘苯 、 环己烷基甲醛 在 苯基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以76%的产率得到(±)-(2-nitrophenyl)cyclohexylmethanol
  参考文献：
  名称：

  Base-modified thymidines capable of terminating DNA synthesis are novel bioactive compounds with activity in cancer cells

  摘要：

  Current FDA-approved chemotherapeutic antimetabolites elicit severe side effects that warrant their improvement; therefore, we designed compounds with mechanisms of action focusing on inhibiting DNA replication rather than targeting multiple pathways. We previously discovered that 5-(alpha-substituted-2-nitrobenzyloxy)methyluridine-5 '-triphosphates were exquisite DNA synthesis terminators; therefore, we synthesized a library of 35 thymidine analogs and evaluated their activity using an MTT cell viability assay of MCF7 breast cancer cells chosen for their vulnerability to these nucleoside derivatives. Compound 3a, having an alpha-tert-butyl-2-nitro-4-(phenyl)alkynylbenzyloxy group, showed an IC50 of 9 +/- 1 mu M. The compound is more selective for cancer cells than for fibroblast cells compared with 5-fluorouracil. Treatment of MCF7 cells with 3a elicits the DNA damage response as indicated by phosphorylation of gamma-H2A. A primer extension assay of the 5 '-triphosphate of 3a revealed that 3aTP is more likely to inhibit DNA polymerase than to lead to termination events upon incorporation into the DNA replication fork. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.057

文献信息

• NOVEL NANOCARRIER DELIVERED CANCER CHEMOTHERAPEUTIC AGENTS
  申请人：UNIVERSITY OF CINCINNATI

  公开号：US20160101188A1

  公开（公告）日：2016-04-14

  Compositions and methods for treating cancer in a subject are described herein. The composition includes modified nucleobases and nucleosides that are converted in the cell to nucleotides that are incorporated into growing DNA and result in termination of DNA elongation. The nucleobases and nucleotides are incorporated with a drug delivery system (DDS). The DDS includes β-cyclodextrin. The nucleobases and nucleotides are conjugated to the β-cyclodextrin by an acid labile linker that releases the nucleobases and nucleotides in the acidic environment of cancer cells. The DDS may also include a targeting ligand that targets the DDS/nucleobase or nucleotide conjugate to cancer cells. The DDS/nucleobase or nucleotide conjugate may self form into nanoparticles and may be administered to a subject with cancer in an amount effective to treat said cancer.

  本文描述了用于治疗患者癌症的组合物和方法。该组合物包括经过修饰的核碱基和核苷，这些核碱基和核苷在细胞中转化为核苷酸，并被合并到正在生长的DNA中，导致DNA延伸终止。这些核碱基和核苷与药物输送系统（DDS）一起使用。DDS包括β-环糊精。核碱基和核苷通过酸敏链连接到β-环糊精上，该链在癌细胞的酸性环境中释放核碱基和核苷。DDS还可以包括靶向配体，将DDS/核碱基或核苷共轭物靶向癌细胞。DDS/核碱基或核苷共轭物可以自行形成纳米粒子，并可以以有效治疗癌症的剂量给患者服用。
• Base-modified thymidines capable of terminating DNA synthesis are novel bioactive compounds with activity in cancer cells
  作者：Kayla M. Borland、Safnas F. AbdulSalam、Morwena J. Solivio、Matthew P. Burke、Patrick R. Wolfkiel、Sean M. Lawson、Courtney A. Stockman、Joel M. Andersen、Skyler Smith、Julia N. Tolstolutskaya、Purujit N. Gurjar、Aron P. Bercz、Edward J. Merino、Vladislav A. Litosh

  DOI：10.1016/j.bmc.2015.01.057

  日期：2015.4

  Current FDA-approved chemotherapeutic antimetabolites elicit severe side effects that warrant their improvement; therefore, we designed compounds with mechanisms of action focusing on inhibiting DNA replication rather than targeting multiple pathways. We previously discovered that 5-(alpha-substituted-2-nitrobenzyloxy)methyluridine-5 '-triphosphates were exquisite DNA synthesis terminators; therefore, we synthesized a library of 35 thymidine analogs and evaluated their activity using an MTT cell viability assay of MCF7 breast cancer cells chosen for their vulnerability to these nucleoside derivatives. Compound 3a, having an alpha-tert-butyl-2-nitro-4-(phenyl)alkynylbenzyloxy group, showed an IC50 of 9 +/- 1 mu M. The compound is more selective for cancer cells than for fibroblast cells compared with 5-fluorouracil. Treatment of MCF7 cells with 3a elicits the DNA damage response as indicated by phosphorylation of gamma-H2A. A primer extension assay of the 5 '-triphosphate of 3a revealed that 3aTP is more likely to inhibit DNA polymerase than to lead to termination events upon incorporation into the DNA replication fork. (C) 2015 Elsevier Ltd. All rights reserved.
• [EN] NOVEL NANOCARRIER DELIVERED CANCER CHEMOTHERAPEUTIC AGENTS<br/>[FR] NOUVEAUX AGENTS CHIMIOTHÉRAPEUTIQUES ANTICANCÉREUX DÉLIVRÉS PAR NANO-PORTEUR
  申请人：UNIV CINCINNATI

  公开号：WO2014194250A3

  公开（公告）日：2015-04-09