2-(3',4'-dichlorophenyl)-1,4-benzoquinone | 174687-52-6

• 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: 2-(3',4'-dichlorophenyl)-1,4-benzoquinone
• 英文别名: 2-(3,4-Dichlorophenyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 174687-52-6
• 化学式: C₁₂H₆Cl₂O₂
• 分子量: 253.084
• InChiKey: HYHPITZFKVCMLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3',4'-dichlorophenyl)-1,4-benzoquinone 在 sodium dithionite 作用下， 以78%的产率得到2-(3',4'-dichlorophenyl)-1,4-hydroquinone
  参考文献：
  名称：

  Oxidative DNA Damage Induced by Activation of Polychlorinated Biphenyls (PCBs):  Implications for PCB-Induced Oxidative Stress in Breast Cancer

  摘要：

  We have previously reported that mono- and dichlorinated biphenyls (PCBs) can be metabolized to dihydroxy compounds and further oxidized to reactive metabolites which form adducts with nitrogen and sulfur nucleophiles including DNA [Amaro et al. (1996) Chem. Res. Toxicol, 9, 623-629; Oakley et al. (1996) Carcinogenesis 17, 109-114]. The former studies also demonstrated that during the metabolism of PCBs superoxide may be produced. We have therefore examined the abilities of PCB metabolites to induce free radical-mediated oxidative DNA damage using a newly developed, highly sensitive, P-32-postlabeling assay for 8-oxode-oxyguanosine (8-oxodG) [Devanaboyina, U., and Gupta, R. (1996) Carcinogenesis 17, 917-924]. The incubation of 3,4-dichloro-2',5'-dihydroxybiphenyl (100 mu M) with calf thymus DNA (300 mu g/mL) in the presence of the breast tissue and milk-associated enzyme, lactoperoxidase (10 mU/mL), and H2O2 (0.5 mM) resulted in a significant increase in free radical-induced DNA damage (253 8-oxodG/10(6) nucleotides) as compared to vehicle-treated DNA (118 8-oxodG/10(6) nucleotides). Substituting CuCl2 (100 mu M) for lactoperoxidase/H2O2, however, resulted in a substantial increase in 8-oxodG content (2669 8-oxodG/10(6) nucleotides). FeCl3 was ineffective, suggesting that CuCl2 but not FeCl3 mediates oxidation of PCB dihydroxy metabolites, resulting in oxidative DNA damage. The addition of catalase (100 U/mL) and sodium azide (0.1 M) reduced the effect of CuCl2 (849 and 896 8-oxodG/10(6) nucleotides, respectively), while superoxide dismutase (600 U/mL) moderately stimulated and glutathione (100 mu M) substantially stimulated 8-oxodG formation (3014 and 4415 8-oxodG/10(6) nucleotides, respectively). The effect of various buffers as well as the effects of PCB structure on Cu(II)-mediated oxidative DNA damage were examined. These results demonstrate that free radicals and oxidative DNA damage are produced during oxidation of lower chlorinated biphenyls. The relevance of the results is discussed in view of the recent report that increased oxidative DNA base damage is detected in the DNA of human breast tumor tissue.

  DOI：

  10.1021/tx960103o
• 作为产物：
  描述：

  2-(3',4'-dichlorophenyl)-1,4-hydroquinone 在 superoxide dismutse (EC 1.15.1.1) 氧气 作用下， 生成 2-(3',4'-dichlorophenyl)-1,4-benzoquinone
  参考文献：
  名称：

  多氯联苯对醌的代谢活化：对氮和硫亲核试剂的反应性和超氧化物歧化酶的影响。

  摘要：

  多氯联苯（PCB）可能会受到细胞色素P-450催化的羟基化作用，从而形成氯化二羟基联苯代谢物。当羟基彼此邻位或对位时，细胞内存在的过氧化物酶可催化氧化成醌。为了研究PCB衍生的醌的反应活性，合成并表征了所选的氯苯基1,2-和1,4-苯醌，包括它们对饱和甘汞电极的还原电位。通过将相应的二羟基联苯与2,3-氧化制得两个醌，即4-（4'-氯苯基）-1,2-和4-（3'，4'-二氯苯基）-1,2-苯醌。二氯-5,6-二氰基-1,4-苯醌。通过Meerwein芳基化反应合成了六个1,4-苯醌：2-（2'-氯苯基）-1,4-，2-（3'-氯苯基）-1,4-，2-（4' -氯苯基）-1,4-，2-（2'，5'-二氯苯基）-1,4-，2-（3'，4'-二氯苯基）-1,4-和2-（3'， 5'-二氯苯基）-1,4-苯醌。作为模型研究，在拟一级条件下确定了2-（4'-氯苯基）-1,4-苯醌对氮亲核试剂甘氨酸，

  DOI：

  10.1021/tx950117e

文献信息

• Metabolic Activation of PCBs to Quinones:  Reactivity toward Nitrogen and Sulfur Nucleophiles and Influence of Superoxide Dismutase
  作者：Anthony R. Amaro、Greg G. Oakley、Udo Bauer、H. Peter Spielmann、Larry W. Robertson

  DOI：10.1021/tx950117e

  日期：1996.1.1

  groups are ortho or para to each other, oxidation to a quinone may be catalyzed by peroxidases present within the cell. In order to study the reactivity of PCB-derived quinones, selected chlorophenyl 1,2- and 1,4-benzoquinones were synthesized and characterized, including their reduction potentials against a saturated calomel electrode. Two quinones, 4-(4'-chlorophenyl)-1,2-, and 4-(3',4'-dichlorophenyl)-1

  多氯联苯（PCB）可能会受到细胞色素P-450催化的羟基化作用，从而形成氯化二羟基联苯代谢物。当羟基彼此邻位或对位时，细胞内存在的过氧化物酶可催化氧化成醌。为了研究PCB衍生的醌的反应活性，合成并表征了所选的氯苯基1,2-和1,4-苯醌，包括它们对饱和甘汞电极的还原电位。通过将相应的二羟基联苯与2,3-氧化制得两个醌，即4-（4'-氯苯基）-1,2-和4-（3'，4'-二氯苯基）-1,2-苯醌。二氯-5,6-二氰基-1,4-苯醌。通过Meerwein芳基化反应合成了六个1,4-苯醌：2-（2'-氯苯基）-1,4-，2-（3'-氯苯基）-1,4-，2-（4' -氯苯基）-1,4-，2-（2'，5'-二氯苯基）-1,4-，2-（3'，4'-二氯苯基）-1,4-和2-（3'， 5'-二氯苯基）-1,4-苯醌。作为模型研究，在拟一级条件下确定了2-（4'-氯苯基）-1,4-苯醌对氮亲核试剂甘氨酸，
• Heterocycles Synthesis Based on Arylation Products of Unsaturated Compounds: XII. Reactions of 2-Aryl-1,4-benzoquinones with Dithiol Compounds
  作者：N. D. Obushak、R. L. Martyak、V. S. Matiichuk

  DOI：10.1007/s11178-005-0238-3

  日期：2005.5

  Reactions of 2-aryl-1,4-benzoquinones with disodium (2,2-dicyano-1,1-ethylene)dithiolate gave rise either to 1,3-benzodithiol or 1,3-benzoxathiol depending on the character of the aryl substituent. 2-Aryl-1,4-benzoquinones reacted with 3-methylsulfanyl-3-sulfanyl-2-cyanoacrylamide with a higher selectivity: 2-(7-Aryl-5-hydroxy-1,3-benzoxathiol-2-ylidene)-2-cyanoacetamides were obtained in a high yield.

  根据芳基取代基的特性，2-芳基-1,4-苯醌与（2,2-二氰基-1,1-乙烯）二硫醇二钠盐反应生成 1,3-苯并二硫醇或 1,3-苯并噁硫醇。2-芳基-1,4-苯醌与 3-甲硫基-3-硫酰基-2-氰基丙烯酰胺的反应选择性更高：可以高产率获得 2-（7-芳基-5-羟基-1,3-苯并恶硫醇-2-亚基）-2-氰基乙酰胺。
• Oxidative DNA Damage Induced by Activation of Polychlorinated Biphenyls (PCBs):  Implications for PCB-Induced Oxidative Stress in Breast Cancer
  作者：Gregory G. Oakley、Udaya-sankar Devanaboyina、Larry W. Robertson、Ramesh C. Gupta

  DOI：10.1021/tx960103o

  日期：1996.1.1

  We have previously reported that mono- and dichlorinated biphenyls (PCBs) can be metabolized to dihydroxy compounds and further oxidized to reactive metabolites which form adducts with nitrogen and sulfur nucleophiles including DNA [Amaro et al. (1996) Chem. Res. Toxicol, 9, 623-629; Oakley et al. (1996) Carcinogenesis 17, 109-114]. The former studies also demonstrated that during the metabolism of PCBs superoxide may be produced. We have therefore examined the abilities of PCB metabolites to induce free radical-mediated oxidative DNA damage using a newly developed, highly sensitive, P-32-postlabeling assay for 8-oxode-oxyguanosine (8-oxodG) [Devanaboyina, U., and Gupta, R. (1996) Carcinogenesis 17, 917-924]. The incubation of 3,4-dichloro-2',5'-dihydroxybiphenyl (100 mu M) with calf thymus DNA (300 mu g/mL) in the presence of the breast tissue and milk-associated enzyme, lactoperoxidase (10 mU/mL), and H2O2 (0.5 mM) resulted in a significant increase in free radical-induced DNA damage (253 8-oxodG/10(6) nucleotides) as compared to vehicle-treated DNA (118 8-oxodG/10(6) nucleotides). Substituting CuCl2 (100 mu M) for lactoperoxidase/H2O2, however, resulted in a substantial increase in 8-oxodG content (2669 8-oxodG/10(6) nucleotides). FeCl3 was ineffective, suggesting that CuCl2 but not FeCl3 mediates oxidation of PCB dihydroxy metabolites, resulting in oxidative DNA damage. The addition of catalase (100 U/mL) and sodium azide (0.1 M) reduced the effect of CuCl2 (849 and 896 8-oxodG/10(6) nucleotides, respectively), while superoxide dismutase (600 U/mL) moderately stimulated and glutathione (100 mu M) substantially stimulated 8-oxodG formation (3014 and 4415 8-oxodG/10(6) nucleotides, respectively). The effect of various buffers as well as the effects of PCB structure on Cu(II)-mediated oxidative DNA damage were examined. These results demonstrate that free radicals and oxidative DNA damage are produced during oxidation of lower chlorinated biphenyls. The relevance of the results is discussed in view of the recent report that increased oxidative DNA base damage is detected in the DNA of human breast tumor tissue.