3-(Anthrachinon-2-yl)-propionsaeure | 82203-74-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-(Anthrachinon-2-yl)-propionsaeure
• 英文别名: 3-(9,10-Dioxoanthracen-2-yl)propanoic acid；3-(9,10-dioxoanthracen-2-yl)propanoic acid
• CAS: 82203-74-5
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: SSWBOJAJGDNYBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(Anthrachinon-2-yl)-propionsaeure 在 sodium hydroxide 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 1-((2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-{[2-(9,10-dioxo-9,10-dihydro-anthracen-2-yl)-ethylamino]-methyl}-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Amide backbone modifications for antisense oligonucleotides carrying potential intercalating substituents: Influence on the thermodynamic stability of the corresponding duplexes with RNA- and DNA- complements

  摘要：

  The synthesis of the amide dimers 3-5 carrying a potential intercalating substituent on the nitrogen atom of the backbone is presented, together with the incorporation of these modifications into oligonucleotides, the resulting melting temperatures (T-m's) of the corresponding duplexes with RNA- and DNA- complements and a summary of molecular modeling studies. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00318-1
• 作为产物：
  描述：

  2-溴甲基蒽醌 在 sodium hydroxide 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 70.0h， 生成 3-(Anthrachinon-2-yl)-propionsaeure
  参考文献：
  名称：

  Amide backbone modifications for antisense oligonucleotides carrying potential intercalating substituents: Influence on the thermodynamic stability of the corresponding duplexes with RNA- and DNA- complements

  摘要：

  The synthesis of the amide dimers 3-5 carrying a potential intercalating substituent on the nitrogen atom of the backbone is presented, together with the incorporation of these modifications into oligonucleotides, the resulting melting temperatures (T-m's) of the corresponding duplexes with RNA- and DNA- complements and a summary of molecular modeling studies. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00318-1

文献信息

• Design, Synthesis and Structure−Activity Relationships of Novel Taxane-Based Multidrug Resistance Reversal Agents
  作者：Iwao Ojima、Christopher P. Borella、Xinyuan Wu、Pierre-Yves Bounaud、Cecilia Fumero Oderda、Matthew Sturm、Michael L. Miller、Subrata Chakravarty、Jin Chen、Qing Huang、Paula Pera、Tracy A. Brooks、Maria R. Baer、Ralph J. Bernacki

  DOI：10.1021/jm049483y

  日期：2005.3.1

  A series of novel taxane-based multidrug resistance (MDR) reversal agents (TRAs) has been designed and synthesized. Structure-activity relationship (SAR) study clearly indicates that modification of the C-7 position with hydrophobic arenecarbonyleinnamoyl groups brings about high potency against drug efflux mediated by P-glycoprotein (P-gp). Six TRAs exhibit ability to modulate a wide range of ATP-binding cassette (ABC) transporters, such as P-gp, multidrug resistance-associated protein 1 (MRP1), and breast cancer resistance protein (BCRP), which may serve as novel broad-spectrum modulators of ABC transporters.