N-acetyl-7-(trifluoroacetamido)-1,2,3,4-tetrahydroisoquinoline | 174648-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: N-acetyl-7-(trifluoroacetamido)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: N-acetyl-7-trifluoroacetamido-1,2,3,4-tetrahydroisoquinoline；N-(2-acetyl-3,4-dihydro-1H-isoquinolin-7-yl)-2,2,2-trifluoroacetamide
• CAS: 174648-91-0
• 化学式: C₁₃H₁₃F₃N₂O₂
• 分子量: 286.254
• InChiKey: MBJXYHWTTVTSEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-acetyl-7-(trifluoroacetamido)-1,2,3,4-tetrahydroisoquinoline 在 盐酸 、 硫酸 、 potassium nitrate 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 22.83h， 生成 1,2,3,4-四氢-6-硝基异喹啉
  参考文献：
  名称：

  Synthesis and Flow Cytometric Evaluation of Novel 1,2,3,4-Tetrahydroisoquinoline Conformationally Constrained Analogues of Nitrobenzylmercaptopurine Riboside (NBMPR) Designed for Probing Its Conformation When Bound to the es Nucleoside Transporter

  摘要：

  Novel regioisomers of conformationally constrained analogues of the potent es nucleoside transporter ligand, nitrobenzylmercaptopurine riboside (NBMPR), designed for probing its bound (bioactive) conformation, were synthesized and evaluated as es transporter ligands by flow cytometry. Purine 6-position 5, 6, 7, or 8-nitro-1,2,3,4-tetrahydroisoquinolylpurine ribosides, in which the nitrobenzyl moiety in NBMPR has been locked into the nitro-1,2,3,4-tetrahydroisoquinoline system, were synthesized by reaction of the appropriate nitro-1,2,3,4-tetrahydroisoquinoline with 6-chloropurine riboside. Flow cytometry was performed using 5-(SAENTA)X8-fluorescein as the competitive ligand. A high degree of variation in the es transporter binding capacity of the target compounds was observed, with the K-i values ranging from 0.45 nM for the most tightly bound compound (4) to 300 nM for the least tightly bound compound (5). The Ki of NBMPR was 0.70 nM, a little higher than that of compound 4. Compound 4 is the isomer that has the nitro group in the best orientation at the es transporter binding site compared to the other three compounds, 2, 3, and 5.

  DOI：

  10.1021/jm020405p
• 作为产物：
  描述：

  1-(7-nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one 在 三氯化铁 、 甲烷 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.58h， 生成 N-acetyl-7-(trifluoroacetamido)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis and Flow Cytometric Evaluation of Novel 1,2,3,4-Tetrahydroisoquinoline Conformationally Constrained Analogues of Nitrobenzylmercaptopurine Riboside (NBMPR) Designed for Probing Its Conformation When Bound to the es Nucleoside Transporter

  摘要：

  Novel regioisomers of conformationally constrained analogues of the potent es nucleoside transporter ligand, nitrobenzylmercaptopurine riboside (NBMPR), designed for probing its bound (bioactive) conformation, were synthesized and evaluated as es transporter ligands by flow cytometry. Purine 6-position 5, 6, 7, or 8-nitro-1,2,3,4-tetrahydroisoquinolylpurine ribosides, in which the nitrobenzyl moiety in NBMPR has been locked into the nitro-1,2,3,4-tetrahydroisoquinoline system, were synthesized by reaction of the appropriate nitro-1,2,3,4-tetrahydroisoquinoline with 6-chloropurine riboside. Flow cytometry was performed using 5-(SAENTA)X8-fluorescein as the competitive ligand. A high degree of variation in the es transporter binding capacity of the target compounds was observed, with the K-i values ranging from 0.45 nM for the most tightly bound compound (4) to 300 nM for the least tightly bound compound (5). The Ki of NBMPR was 0.70 nM, a little higher than that of compound 4. Compound 4 is the isomer that has the nitro group in the best orientation at the es transporter binding site compared to the other three compounds, 2, 3, and 5.

  DOI：

  10.1021/jm020405p

文献信息

• Hypoxia-Selective Antitumor Agents. 12. Nitrobenzyl Quaternary Salts as Bioreductive Prodrugs of the Alkylating Agent Mechlorethamine
  作者：Moana Tercel、William R. Wilson、Robert F. Anderson、William A. Denny

  DOI：10.1021/jm9507791

  日期：1996.1.1

  -358 mV and undergoes reductively-induced fragmentation to release the nitrogen mustard mechlorethamine. The compounds were prepared by halogenation (SOCl2) of the corresponding quaternary diols, which in turn were synthesized from N-methyldiethalnolamine and substituted nitrobenzyl chlorides. The reduction potentials of the benzene-substituted compounds were generally well-predicted by Hammett substituent

  新型低氧选择性细胞毒素N，N-双（2-氯乙基）-N-甲基-N-（2-硝基苄基）氯化铵（3a）的一系列苯取代类似物，以及三个相应的“环”四氢异喹啉鎓已经制备了类似物21a-23a和两种萘衍生物（19a和20a），并在有氧和低氧条件下评估了培养的哺乳动物肿瘤细胞的细胞毒性。母体化合物3a的单电子还原电势为-358mV，并经历还原诱导的裂解以释放芥菜甲氧乙胺氮。该化合物是通过相应的季二醇的卤化（SOCl2）制备的，而这些季二醇又是由N-甲基二乙二胺和取代的硝基苄基氯合成的。苯取代的化合物的还原电势通常通过哈米特取代基关系很好地预测。所有化合物对修复缺陷型UV4细胞的毒性都比相应的野生型AA8细胞高得多，这是预期的，如果活性细胞毒性物质用作DNA烷基化剂。与AA8相比，它们对人细胞EMT6和FME的毒性更大，但其原因尚不清楚。在苯环中被给电子取代基取代的3a类似物为低氧AA8细胞提供了广泛不同的选
• Novel Nucleoside Transport Inhibitors
  申请人：Buolamwini Kwesi John

  公开号：US20070293444A1

  公开（公告）日：2007-12-20

  Compounds or compositions that are inhibitors and/or ligands of nucleoside transporters; and methods of treating cancer, heart disease and stroke, as well as AIDS and other infectious diseases

  抑制核苷酸转运体的化合物或组合物；以及治疗癌症、心脏病和中风，以及艾滋病和其他传染病的方法。
• Nucleoside transport inhibitors
  申请人：Quesrema Enterprises LLC

  公开号：US07582616B2

  公开（公告）日：2009-09-01

  Compounds or compositions that are inhibitors and/or ligands of nucleoside transporters; and methods of treating cancer, heart disease and stroke, as well as AIDS and other infectious diseases.

  抑制核苷酸转运体的化合物或组合物；以及治疗癌症、心脏病和中风，以及艾滋病和其他传染病的方法。
• [EN] NOVEL NUCLEOSIDE TRANSPORT INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DU TRANSPORT DES NUCLEOSIDES
  申请人：BUOLAMWINI JOHN K

  公开号：WO2004060902A3

  公开（公告）日：2004-10-07
• US7582616B2
  申请人：——

  公开号：US7582616B2

  公开（公告）日：2009-09-01