bis(trifluoromethyl) carbonate | 5659-86-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: bis(trifluoromethyl) carbonate
• 英文别名: TFAA；Carbonic acid bis(trifluoromethyl) ester
• CAS: 5659-86-9
• 化学式: C₃F₆O₃
• 分子量: 198.022
• InChiKey: LVYPNDZTRXRBNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  bis(trifluoromethyl) carbonate 、 N-(6-ethoxybenzo[d]thiazol-2-yl)-2-((4-fluorophenyl)amino)nicotinamide 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.17h， 以80%的产率得到3-(6-ethoxybenzo[d]thiazol-2-yl)-1-(4-fluorophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and anticancer potential of benzothiazole linked phenylpyridopyrimidinones and their diones as mitochondrial apoptotic inducers

  摘要：

  A series of benzothiazole linked phenylpyridopyrimidinones (8a-g) and their diones (9a-g) have been designed, synthesized and evaluated for their anticancer activity. Among the series one of the conjugate 8b showed significant cytotoxicity against human cervical cancer cell line ME-180 with IC50 value of 4.01 mu M. This compound was tested on the cell cycle perturbations and DNA damage. Flow cytometry analysis revealed that the compound 8b showed drastic cell cycle perturbations due to concentration dependent increase in the sub-G0 phase in ME-180 cell line. DNA fragmentation and Hoechst staining reveals that this compound induced cell death by apoptosis. Further caspase-3 and loss of mitochondrial membrane potential suggested that the compound induces cell death by apoptosis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.057
• 作为产物：
  描述：

  三氟甲基次氟酸酯 、 一氧化碳 、 perfluoro-4-methyl-2-pentene 以91.4%的产率得到Trifluormethyl-fluorformiat
  参考文献：
  名称：

  由三氟甲基次萤石和一氧化碳合成氟甲酸三氟甲酯：热催化反应

  摘要：

  开发了新的和改进的途径来制备三氟甲基氟甲酸酯。立体位阻卤代烯烃在温和条件下引发了CF 3 OF和CO的反应，产率高达80％。CF 3 OF和CO在流动系统中的热反应高度依赖于温度和管式反应器材料的类型。PTFE反应器在120°C下对甲酸酯具有中等转化率和较高的选择性。

  DOI：

  10.1016/j.jfluchem.2009.07.004
• 作为试剂：
  描述：

  4,5-二氯-2-(四氢-吡喃-2-基)-2H-吡嗪-3-酮 在 bis(trifluoromethyl) carbonate 、 水 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-羰基二咪唑 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 生成 5-[5-chloro-1-(oxan-2-yl)-6-oxo-1,6-dihydropyridazin-4-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-3-carbonitrile
  参考文献：
  名称：

  [EN] PYRIDAZINONES AND METHODS OF USE THEREOF
  [FR] PYRIDAZINONES ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2019055966A3

文献信息

• Identification of novel indole derivatives as highly potent and efficacious LSD1 inhibitors
  作者：Xiangyu Zhang、Yixiang Sun、Hailan Huang、Xinran Wang、Tianxiao Wu、Wenbo Yin、Xiaojia Li、Lin Wang、Yanting Gu、Dongmei Zhao、Maosheng Cheng

  DOI：10.1016/j.ejmech.2022.114523

  日期：2022.9

  demethylase to catalyze the demethylation of H3K4 and H3K9 and thus is an attractive target for therapeutic cancer. Starting with a high micromolar compound 17i, structure-based optimization of novel indole derivatives is described by a bioelectronic isosteric strategy. Grounded by molecular modeling, medicinal chemistry has efficiently yielded low nanomolar LSD1 inhibitors. One of the compounds, B35, exhibited

  赖氨酸特异性去甲基化酶 1 (LSD1) 是一种 FAD 依赖性组蛋白去甲基化酶，可催化 H3K4 和 H3K9 去甲基化，因此是治疗癌症的一个有吸引力的靶点。从高微摩尔化合物17i开始，通过生物电子等排策略描述了新型吲哚衍生物的基于结构的优化。以分子模型为基础，药物化学有效地产生了低纳摩尔 LSD1 抑制剂。其中一种化合物B35对 A549 细胞表现出优异的 LSD1 抑制作用 (IC 50 = 0.050 ± 0.005 μM ) 和抗增殖作用 (IC 50 = 0.74 ± 0.14 μM )。进一步的PK研究表明化合物B35具有良好的代谢稳定性，po和iv的血浆t 1/2分别为6.27±0.72 h和8.78±1.31 h。此外，抑制剂B35具有很强的抗肿瘤作用和良好的体内安全性。同时，化合物B35调节的基因与癌症中的转录错位以及涉及IGFBP3的PI3K/AKT通路密切相关。总而言之，
• Tumor‐Selective Activation of Toll‐Like Receptor 7/8 Agonist Nano‐Immunomodulator Generates Safe Anti‐Tumor Immune Responses upon Systemic Administration
  作者：Yanyun Hao、Hui Li、Xiaoyan Ge、Yang Liu、Xia Li、Yutong Liu、Hongfei Chen、Shiying Zhang、Jing Zou、Lingling Huang、Fabao Zhao、Dongwei Kang、Bruno G. De Geest、Zhiyue Zhang

  DOI：10.1002/anie.202214992

  日期：2022.12.23

  To overcome the uncontrolled off-target systemic immune-related adverse effects (irAEs) of imidazoquinolines after systemic administration, we developed a nano-immunomodulator (cN@SS-IMQ) that is inactive until it is selectively metabolized to an active immunostimulant within tumor cells. cN@SS-IMQ promoted robust immune activation within tumors while limiting extra-tumoral stimulation, suggesting

  为了克服全身给药后咪唑喹啉的不受控制的脱靶全身免疫相关不良反应 (irAEs)，我们开发了一种纳米免疫调节剂 (cN@SS-IMQ)，它在肿瘤细胞内被选择性代谢为活性免疫刺激剂之前是无活性的. cN@SS-IMQ 在限制肿瘤外刺激的同时促进了肿瘤内的强大免疫激活，表明其在系统靶向先天免疫肿瘤刺激物方面具有广阔的潜力。
• <i>N</i>-Methylsansalvamide A Peptide Analogues. Potent New Antitumor Agents
  作者：Shouxin Liu、Wenxin Gu、Denise Lo、Xian-Zhong Ding、Michael Ujiki、Thomas E. Adrian、Gerald A. Soff、Richard B. Silverman

  DOI：10.1021/jm048952t

  日期：2005.5.1

  Sansalvamide A, a cyclic depsipeptide isolated from a marine fungus of the genus Fusarium, is composed of four hydrophobic amino acids (Phe, two Leu, Val) and one hydroxy acid ((S)2-hydroxy-4-methylpentanoic acid; O-Leu) with five stereogenic centers all having S-stereochemistry. We have recently synthesized the corresponding cyclic peptide (Gu, W.; Liu, S.; Silverman, R. B. Organic Lett. 2002,4, 4171-4174) and found that it too has antitumor activity. N-Methylation can enhance potency and selectivity for peptides. Consequently, here we synthesize 12 different N-methylated sansalvamide A peptide analogues and show that for several different tumor cell lines three of these analogues are more potent than the natural product; in pancreatic cells, sansalvamide A shows little activity, but the N-methylsansalvamide peptides are potent cytotoxic agents.
• Synthesis and anticancer potential of benzothiazole linked phenylpyridopyrimidinones and their diones as mitochondrial apoptotic inducers
  作者：Ähmed Kamal、Md. Ashraf、M.V.P.S. Vishnu Vardhan、Shaikh Faazil、V. Lakshma Nayak

  DOI：10.1016/j.bmcl.2013.11.057

  日期：2014.1

  A series of benzothiazole linked phenylpyridopyrimidinones (8a-g) and their diones (9a-g) have been designed, synthesized and evaluated for their anticancer activity. Among the series one of the conjugate 8b showed significant cytotoxicity against human cervical cancer cell line ME-180 with IC50 value of 4.01 mu M. This compound was tested on the cell cycle perturbations and DNA damage. Flow cytometry analysis revealed that the compound 8b showed drastic cell cycle perturbations due to concentration dependent increase in the sub-G0 phase in ME-180 cell line. DNA fragmentation and Hoechst staining reveals that this compound induced cell death by apoptosis. Further caspase-3 and loss of mitochondrial membrane potential suggested that the compound induces cell death by apoptosis. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of trifluoromethyl fluoroformate from trifluoromethyl hypofluorite and carbon monoxide: Thermal and catalyzed reaction
  作者：Libin Du、Darryl D. DesMarteau、V. Tortelli、M. Galimberti

  DOI：10.1016/j.jfluchem.2009.07.004

  日期：2009.9

  New and improved routes to trifluoromethyl fluoroformate were developed. Sterically hindered halogenated olefins initiated the reaction of CF3OF and CO under mild conditions, giving yields of up to 80%. The thermal reaction of CF3OF and CO in a flow system was highly dependent on temperature and the type of tubular reactor material. A PTFE reactor gave moderate conversion and high selectivity for the

  开发了新的和改进的途径来制备三氟甲基氟甲酸酯。立体位阻卤代烯烃在温和条件下引发了CF 3 OF和CO的反应，产率高达80％。CF 3 OF和CO在流动系统中的热反应高度依赖于温度和管式反应器材料的类型。PTFE反应器在120°C下对甲酸酯具有中等转化率和较高的选择性。