3-(1,4-dihydro-2-methyl-1,4-dioxo-naphthalen-3-yl-thio)propionic acid | 6325-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1,4-dihydro-2-methyl-1,4-dioxo-naphthalen-3-yl-thio)propionic acid
• 英文别名: (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl-sulfanyl)acetic acid；(3-methyl-1,4-dioxo-1,4-dihydro-[2]naphthylsulfanyl)-acetic acid；(3-Methyl-1,4-dioxo-1,4-dihydro-[2]naphthylmercapto)-essigsaeure；S-<3-Methyl-1,4-naphtochinon-2-yl>-thioglykolsaeure；[(3-Methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid；2-(3-methyl-1,4-dioxonaphthalen-2-yl)sulfanylacetic acid
• CAS: 6325-58-2
• 化学式: C₁₃H₁₀O₄S
• 分子量: 262.286
• InChiKey: XATVOMBATOYURF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  96.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(1,4-dihydro-2-methyl-1,4-dioxo-naphthalen-3-yl-thio)propionic acid 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 甲萘醌
  参考文献：
  名称：

  醌。第四部分 消除1：4-萘醌中的取代基

  摘要：

  DOI：

  10.1039/jr9540001428
• 作为产物：
  描述：

  2-methyl-5,8-dihydro-1,4-naphthalenediol 在 chromium(VI) oxide 、 potassium dichromate 、 乙醚 、 硫酸 、 溴 、 溶剂黄146 、 sodium iodide 作用下， 生成 3-(1,4-dihydro-2-methyl-1,4-dioxo-naphthalen-3-yl-thio)propionic acid
  参考文献：
  名称：

  Andrews et al., Journal of the Chemical Society, 1956, p. 1844,1850

  摘要：

  DOI：

文献信息

• 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
• Synthesis and SAR study of novel anticancer and antimicrobial naphthoquinone amide derivatives
  作者：Thonthula Sreelatha、Subramani Kandhasamy、Raghu Dinesh、Suresh Shruthy、Sinha Shweta、Doble Mukesh、Devarajan Karunagaran、Ravichandran Balaji、Narayanasamy Mathivanan、Paramasivan Thirumalai Perumal

  DOI：10.1016/j.bmcl.2014.04.080

  日期：2014.8

  A series of novel naphthoquinone amide derivatives of the bioactive quinones, plumbagin, juglone, menadione and lawsone, with various amino acids were synthesized. The compounds were characterized by H-1 NMR, C-13 NMR, Mass, IR and elemental analysis. All the compounds were evaluated for their anticancer activity against HeLa and SAS cancer cell lines and 3D-QSAR indicated the presence of electron donating group near sulphur enhanced the activity against HeLa cells. Among the derivatives synthesized, compounds 11f, 10a, 10b and 10g were the most active with IC50 values of 16, 12, 14 and 24.5 mu M respectively. The analogues were also screened for antimicrobial activity against two human bacterial pathogens, the Gram-positive Methicillin resistant Staphylococcus aureus (MRSA) and the Gram-negative Pseudomonas aeruginosa and a human yeast pathogen, Fluconazole resistant Candida albicans (FRCA). Among the synthesized compounds, 8g, 10g and 11g exhibited maximum antibacterial activity towards MRSA and antifungal activity against FRCA in well diffusion method. (C) 2014 Elsevier Ltd. 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.
• Naphthoquinone Acids and Ketols¹
  作者：Louis F. Fieser、Richard B. Turner

  DOI：10.1021/ja01202a026

  日期：1947.10
• CHEMICAL AGENTS FOR THE PREVENTION OF INHIBITION OR TUMOR METASTASIS
  申请人：Bresnick Anne R.

  公开号：US20130090355A1

  公开（公告）日：2013-04-11

  The present invention provides methods of preventing or inhibiting tumor metastasis in a subject by administering a therapeutically effective amount of (1) a compound from a group of enumerated compounds, or a pharmaceutically acceptable salt thereof; (2) an agent that covalently modifies at least one cysteine residue of S100A4 protein; or (3) an agent that inhibits the interaction between S100A4 and myosin-IIA.