2,3-双(疏基乙酸)-1,4-萘二酮 | 108900-05-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2,3-双(疏基乙酸)-1,4-萘二酮
• 英文名称: (3-carboxymethylsulfanyl-1,4-dioxo-1,4-dihydro-naphthalen-2-ylsyfanyl) acetic acid
• 英文别名: 2,3-Bis(mercaptoacetic acid)-1,4-naphthalenedione；2-[3-(carboxymethylsulfanyl)-1,4-dioxonaphthalen-2-yl]sulfanylacetic acid
• CAS: 108900-05-6
• 化学式: C₁₄H₁₀O₆S₂
• mdl: MFCD06656509
• 分子量: 338.362
• InChiKey: DLPXDGDDLLFSPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3-双(疏基乙酸)-1,4-萘二酮 、 三苯基氧化膦 以 甲醇 为溶剂， 以61%的产率得到
  参考文献：
  名称：

  Characterization of Molecular Complexes of 1,4-Naphthoquinone Derivatives

  摘要：

  含柔性羧酸(3-甲基-1,4-二氧代-1,4-二氢萘-2-基硫基)乙酸(1)的硫原子束缚醌的结构及其与4,4'-联吡啶的分子配合物(3 ) 确定。化合物 1 在 P-1 中结晶（三斜晶系，a = 7.5378(6) Å, b = 7.6413(7) Å, c = 10.3101(9) Å; α = 89.779 (7)°, β = 81.042 (5)° , γ = 89.101(7)°) 和分子复合物3 分别以 P2(1)/n（单斜晶系，a = 9.3383(7) Å、b = 3.970(3) Å、c = 42.130(3) Å、β = 91.056(5)°）空间群结晶。母体化合物1中存在的二羧酸基团之间的R 2 2 (8)型氢键在与4, 4'-联吡啶相互作用时消失；在分子复合物 3 R 2 2 (7) 中，吡啶环和羧酸基团之间存在 O·H–C 和 O–H·N 型相互作用。由3-羧甲基硫基-1,4-二羟基萘-2-基-硫基)乙酸(2)与氧化三苯基膦按1:2比例衍生得到的分子络合物(4)，在C2/c空间群中结晶，具有单斜晶系，a = 26.0494(13) Å, b = 10.5402(5) Å, c=17.1023(8)Å，β=108.719(5)°)。三苯基氧化膦分子优先由羧酸和P=O键之间的O-H…O相互作用固定。 (3-甲基-1,4-二氧代-1,4-二氢萘-2-基硫基)乙酸及其与4,4'-联吡啶的分子配合物和3-羧甲基硫基-1,4-二羟基分子配合物的结构提出了萘-2-基-硫基）乙酸与三苯基氧化膦

  DOI：

  10.1007/s10870-011-0024-8
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 巯基乙酸 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以89%的产率得到2,3-双(疏基乙酸)-1,4-萘二酮
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity

  摘要：

  CDC25 dual-specificity phosphatases are essential key regulators of eukaryotic cell cycle progression and the CDC25A and B isoforms are over-expressed in different tumors and related cancer cell lines. CDC25s are now considered to be interesting targets in the search for novel anticancer agents. We describe new compounds derived from vitamin K-3 that inhibit CDC25B activity with IC50 values in the low micromolar range. These naphthoquinone derivatives also display antiproliferative activity on HeLa cells as expected for CDC25 inhibitors and inhibit cell growth in a clonogenic assay at submicromolar concentrations. They increase inhibitory tyrosine 15 phosphorylation of CDK and induce the cleavage of PARP, a hallmark of apoptosis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.005

文献信息

• Copper(II) complexes of 2-(1,4-dihydro-2-hydroxy-1,4-dioxonaphthalen-3-ylthio) acetic acid
  作者：W. Marjit Singh、Jubaraj B. Baruah

  DOI：10.1016/j.inoche.2010.04.012

  日期：2010.8

  Selective carbon-sulphur bond cleavage reaction of (3-mercapto-1,4-dioxo-1,4-dihydro-naphthalen-2-ylsulfanyl) acetic acid by copper(II) nitrate tetrahydrate at room temperature to form copper(II) complex of 2-(1,4-dihydro-2-hydroxy-1,4-dioxonaphthalen-3-ylthio) acetic acid is described. (C) 2010 Elsevier B.V. All rights reserved.
• Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity
  作者：Marie-Priscille Brun、Emmanuelle Braud、Delphine Angotti、Odile Mondésert、Muriel Quaranta、Matthieu Montes、Maria Miteva、Nohad Gresh、Bernard Ducommun、Christiane Garbay

  DOI：10.1016/j.bmc.2005.05.005

  日期：2005.8

  CDC25 dual-specificity phosphatases are essential key regulators of eukaryotic cell cycle progression and the CDC25A and B isoforms are over-expressed in different tumors and related cancer cell lines. CDC25s are now considered to be interesting targets in the search for novel anticancer agents. We describe new compounds derived from vitamin K-3 that inhibit CDC25B activity with IC50 values in the low micromolar range. These naphthoquinone derivatives also display antiproliferative activity on HeLa cells as expected for CDC25 inhibitors and inhibit cell growth in a clonogenic assay at submicromolar concentrations. They increase inhibitory tyrosine 15 phosphorylation of CDK and induce the cleavage of PARP, a hallmark of apoptosis. (c) 2005 Elsevier Ltd. All rights reserved.
• Characterization of Molecular Complexes of 1,4-Naphthoquinone Derivatives
  作者：W. Marjit Singh、Jubaraj B. Baruah

  DOI：10.1007/s10870-011-0024-8

  日期：2011.7

  The structures of sulphur atom tethered quinone containing flexible carboxylic acid (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylsulfanyl)acetic acid (1) and its molecular complex with 4,4′-bipyridine (3) are determined. The compound 1 crystallizes in P-1 (triclinic, a = 7.5378(6) Å, b = 7.6413(7) Å, c = 10.3101(9) Å; α = 89.779 (7)°, β = 81.042 (5)°, γ = 89.101(7)°) and the molecular complex 3 crystallises in P2(1)/n (monoclinic, a = 9.3383(7) Å, b = 3.970(3) Å, c = 42.130(3) Å, β = 91.056(5)°) space groups, respectively. The R 2 2 (8) type hydrogen bonding between dicarboxylic acid groups present in the parent compound 1 is lost on interaction with 4, 4′-bipyridine; in the molecular complex 3 R 2 2 (7) type of O···H–C and O–H···N interactions are present between the pyridine rings and carboxylic acid groups. The molecular complex (4) derived from 3-carboxymethylsulfanyl-1,4-dihydroxynaphthalen-2-yl-sulfanyl) acetic acid (2) with triphenylphosphine oxide in 1:2 ratio, crystallises in C2/c space group have monoclinic, a = 26.0494(13) Å, b = 10.5402(5) Å, c = 17.1023(8) Å, β = 108.719 (5)°). The triphenylphosphine oxide molecules are preferentially held by O–H···O interactions between carboxylic acid and P=O bond. The structures of (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylsulfanyl) acetic acid , its molecular complex with 4,4′-bipyridine and molecular complex of 3-carboxymethylsulfanyl-1,4-dihydroxy naphthalen-2-yl-sulfanyl)acetic acid with triphenylphosphine oxide are presented

  含柔性羧酸(3-甲基-1,4-二氧代-1,4-二氢萘-2-基硫基)乙酸(1)的硫原子束缚醌的结构及其与4,4'-联吡啶的分子配合物(3 ) 确定。化合物 1 在 P-1 中结晶（三斜晶系，a = 7.5378(6) Å, b = 7.6413(7) Å, c = 10.3101(9) Å; α = 89.779 (7)°, β = 81.042 (5)° , γ = 89.101(7)°) 和分子复合物3 分别以 P2(1)/n（单斜晶系，a = 9.3383(7) Å、b = 3.970(3) Å、c = 42.130(3) Å、β = 91.056(5)°）空间群结晶。母体化合物1中存在的二羧酸基团之间的R 2 2 (8)型氢键在与4, 4'-联吡啶相互作用时消失；在分子复合物 3 R 2 2 (7) 中，吡啶环和羧酸基团之间存在 O·H–C 和 O–H·N 型相互作用。由3-羧甲基硫基-1,4-二羟基萘-2-基-硫基)乙酸(2)与氧化三苯基膦按1:2比例衍生得到的分子络合物(4)，在C2/c空间群中结晶，具有单斜晶系，a = 26.0494(13) Å, b = 10.5402(5) Å, c=17.1023(8)Å，β=108.719(5)°)。三苯基氧化膦分子优先由羧酸和P=O键之间的O-H…O相互作用固定。 (3-甲基-1,4-二氧代-1,4-二氢萘-2-基硫基)乙酸及其与4,4'-联吡啶的分子配合物和3-羧甲基硫基-1,4-二羟基分子配合物的结构提出了萘-2-基-硫基）乙酸与三苯基氧化膦