4,4’-bis(2-chloroacetamido)diphenylmethane | 17328-15-3

• 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: 4,4’-bis(2-chloroacetamido)diphenylmethane
• 英文别名: Di-(p-chloracetamidophenyl)-methan；4,4'-Bis-(chloroacetylamino)-diphenylmethan；N,N'-(4,4'-methylene-bis(1,4-phenylene))bis(2-chloroacetamide)；N,N'-[Methylenedi(4,1-phenylene)]bis(2-chloroacetamide)；2-chloro-N-[4-[[4-[(2-chloroacetyl)amino]phenyl]methyl]phenyl]acetamide
• CAS: 17328-15-3
• 化学式: C₁₇H₁₆Cl₂N₂O₂
• 分子量: 351.232
• InChiKey: SVQWRVUVTZFTFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4’-bis(2-chloroacetamido)diphenylmethane 在 sodium azide 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.01h， 生成 2-[4-[3-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxypropyl]triazol-1-yl]-N-[4-[[4-[[2-[4-[3-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxypropyl]triazol-1-yl]acetyl]amino]phenyl]methyl]phenyl]acetamide
  参考文献：
  名称：

  Size-Specific Ligands for RNA Hairpin Loops

  摘要：

  The targeting of one mRNA in the transcriptome requires small molecules that bind with substantial affinity and specificity. As such, compounds with specificity for individual RNA secondary structural motifs could be useful for targeting RNA. Described herein is the synthesis of a combinatorial library of 105 dimers of deoxystreptamine and the subsequent identification of compounds with specificity for specific RNA hairpin loop sizes, including tetraloops and octaloops. Such compounds will be useful for the perturbation of RNA function in vivo.

  DOI：

  10.1021/ja051685b
• 作为产物：
  描述：

  4,4'-二氨基二苯甲烷 、 氯乙酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以75%的产率得到4,4’-bis(2-chloroacetamido)diphenylmethane
  参考文献：
  名称：

  In Vitro Imaging and Human Serum Albumin Responsive Dimeric Lanthanide DO3A Complex

  摘要：

  Two series of dimeric DO3A (1,4,7,10-tetraazacyclodecane-1,4,7-triacetate) lanthanide complexes (LnL(1)-LnL(2), Ln = Eu, Gd, and Tb) have been synthesized with two different bridged chromophores. The X-ray structures of dimeric LnL(1) (Ln = Gd and Tb) complexes show that each metal ion has nine coordination numbers with eight directly bound donor atoms of the ligand and one oxygen donor from the water molecule. Photophysical measurements indicate that the bridged antenna in LnL(2) gives a higher efficiency than that of LnL(1) and is responsive to the protein Human Serum Albumin (HSA), giving an f-f luminescence signal enhancement with a binding constant log K = 4.84. In vitro imaging of EuL(1) and EuL(2) in HeLa cells has been recorded, and EuL(2) has demonstrated a higher rate of cellular uptake and low cytotoxicity (IC(50) = 3 mM).

  DOI：

  10.1021/ic2004672

文献信息

• New binuclear dithiocarbamate complexes [M₂-µ²-bis-{(κ²S,S-S₂CN(R)CH₂CONHC₆H₄)₂CH₂}] (M=Ni^II, Cu^II, and Zn^II): synthesis, characterization, DFT, and<i>in vitro</i>cytotoxic study
  作者：Vinay K. Singh、Vineeta Pillai、Prakash Gohil、Shailykumari K. Patel、Lipi Buch

  DOI：10.1080/00958972.2018.1525610

  日期：2018.11.17

  A new series of binuclear dithiocarbamate macrocyclic complexes [M-2-mu(2)-bis-(kappa S-2,S-S2CN(R)CH2CONHC6H4)(2)CH2}] R=Cy, M = Ni-II 1a, Cu-II 1b, Zn-II 1c; R=Pr-i, M = Ni-II 2a, Cu-II 2b, Zn-II 2c; R=Bu-n, M = Ni-II 3a, Cu-II 3b, Zn-II 3c} have been efficiently synthesized by using a self-assembly process involving diamino precursor 4,4'-bis(2-(alkylamino)acetamido) diphenylmethane (L-1, L-2, or L-3), CS2 and Ni-II, Cu-II, or Zn-II ion. Compounds are suitably characterized by H-1, C-13, DEPT135, H-1 DOSY NMR, HRMS, ESI MS, UV-Visible absorption, IR, and TGA/DTA methods. The experimental results are further supported by DFT level calculations. Compounds have been screened for their in vitro cytotoxicity against HepG2 (hepatoma) cell line by the MTT assay. The results showed much better activity of all the newly synthesized derivatives than clinically used drug cisplatin and specificity (except L') for cancer cells over normal liver cells. Exceptionally, macrocyclic dithiocarbamate complexes 1b (IC50: 6.91 mu M +/- 0.22 mu M) and 1c (IC50: 5 mu M +/- 0.16 mu M) holding N-Cy substituents showed nearly 10-15 fold better cytotoxic activity against HepG2 cell lines compared to the reference drug cisplatin (IC50: 75.67 mu M +/- 0.25 mu M). The shrinking of cells can be clearly visualized by acridine orange/ethidium bromide (AO/EB) staining, indicating the induction of apoptosis as part of the mechanism of action of these compounds.[GRAPHICS].
• US3939122A
  申请人：——

  公开号：US3939122A

  公开（公告）日：1976-02-17
• Size-Specific Ligands for RNA Hairpin Loops
  作者：Jason R. Thomas、Xianjun Liu、Paul J. Hergenrother

  DOI：10.1021/ja051685b

  日期：2005.9.1

  The targeting of one mRNA in the transcriptome requires small molecules that bind with substantial affinity and specificity. As such, compounds with specificity for individual RNA secondary structural motifs could be useful for targeting RNA. Described herein is the synthesis of a combinatorial library of 105 dimers of deoxystreptamine and the subsequent identification of compounds with specificity for specific RNA hairpin loop sizes, including tetraloops and octaloops. Such compounds will be useful for the perturbation of RNA function in vivo.
• In Vitro Imaging and Human Serum Albumin Responsive Dimeric Lanthanide DO3A Complex
  作者：Yuen On Fung、Wanqing Wu、Chi-Tung Yeung、Hoi-Kuan Kong、Kenny Kam-Cheng Wong、Wai-Sum Lo、Ga-Lai Law、Ka-Leung Wong、Chi-Kong Lau、Chi-Sing Lee、Wing-Tak Wong

  DOI：10.1021/ic2004672

  日期：2011.6.20

  Two series of dimeric DO3A (1,4,7,10-tetraazacyclodecane-1,4,7-triacetate) lanthanide complexes (LnL(1)-LnL(2), Ln = Eu, Gd, and Tb) have been synthesized with two different bridged chromophores. The X-ray structures of dimeric LnL(1) (Ln = Gd and Tb) complexes show that each metal ion has nine coordination numbers with eight directly bound donor atoms of the ligand and one oxygen donor from the water molecule. Photophysical measurements indicate that the bridged antenna in LnL(2) gives a higher efficiency than that of LnL(1) and is responsive to the protein Human Serum Albumin (HSA), giving an f-f luminescence signal enhancement with a binding constant log K = 4.84. In vitro imaging of EuL(1) and EuL(2) in HeLa cells has been recorded, and EuL(2) has demonstrated a higher rate of cellular uptake and low cytotoxicity (IC(50) = 3 mM).