N-acetyl-7-trifluoroacetamido-8-nitro-1,2,3,4-tetrahydroisoquinoline | 724783-85-1

• 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-8-nitro-1,2,3,4-tetrahydroisoquinoline
• 英文别名: N-(2-acetyl-8-nitro-3,4-dihydro-1H-isoquinolin-7-yl)-2,2,2-trifluoroacetamide
• CAS: 724783-85-1
• 化学式: C₁₃H₁₂F₃N₃O₄
• 分子量: 331.251
• InChiKey: QDOSDSNBKFDOLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 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：
  95.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-acetyl-7-trifluoroacetamido-6-nitro-1,2,3,4-tetrahydroisoquinoline 、 N-acetyl-7-trifluoroacetamido-8-nitro-1,2,3,4-tetrahydroisoquinoline 在 盐酸 、 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 0.83h， 以30%的产率得到N-乙酰基-7-氨基-6-硝基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  [EN] NOVEL NUCLEOSIDE TRANSPORT INHIBITORS
  [FR] NOUVEAUX INHIBITEURS DU TRANSPORT DES NUCLEOSIDES

  摘要：

  公开号：

  WO2004060902A3
• 作为产物：
  描述：

  1-(7-nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one 在 硫酸 、 三氯化铁 、 甲烷 、 potassium nitrate 、 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-8-nitro-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

• 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。
• US7582616B2
  申请人：——

  公开号：US7582616B2

  公开（公告）日：2009-09-01
• 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 <i>e</i><i>s</i> Nucleoside Transporter
  作者：Zhengxiang Zhu、John Furr、John K. Buolamwini

  DOI：10.1021/jm020405p

  日期：2003.2.1

  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.
• [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