(7S,8R,9S,10R)-7,8,9,10-四氢-9,10-环氧苯并[a]芘-7,8-二醇 | 63323-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: (7S,8R,9S,10R)-7,8,9,10-四氢-9,10-环氧苯并[a]芘-7,8-二醇
• 英文名称: (+)-(7S,8R,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• 英文别名: benzopyrene (+)-(7S,8R)-diol (9S,10R)-epoxide；benzo[a]pyrene (+)-(7S,8R)-diol (9S,10R)-epoxide；Benzo(a)pyrene-7,8-dihydrodiol 9,10-epoxide, syn-(+)-；(3R,5S,6R,7S)-4-oxahexacyclo[11.6.2.02,8.03,5.010,20.017,21]henicosa-1(20),2(8),9,11,13(21),14,16,18-octaene-6,7-diol
• CAS: 63323-29-5；58917-91-2
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: DQEPMTIXHXSFOR-NMLBUPMWSA-N

物化性质

• 沸点：
  403.36°C (rough estimate)
• 密度：
  1.1653 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

SDS

反应信息

• 作为反应物：
  描述：

  (7S,8R,9S,10R)-7,8,9,10-四氢-9,10-环氧苯并[a]芘-7,8-二醇 生成 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-[[(7R,8R,9S,10R)-7,8,9-trihydroxy-7,8,9,10-tetrahydrobenzo[a]pyren-10-yl]amino]-3H-purin-6-one
  参考文献：
  名称：

  SAYER, JANE M.;CHADHA, ANJU;AGARWAL, SHIV K.;YEH, HERMAN J. C.;YAGI, HARU+, J. ORG. CHEM., 56,(1991) N, C. 20-29

  摘要：

  DOI：
• 作为产物：
  描述：

  7,8-二羟基-7,8-二氢-苯并(a)芘 生成 (7S,8R,9S,10R)-7,8,9,10-四氢-9,10-环氧苯并[a]芘-7,8-二醇
  参考文献：
  名称：

  FU P. P.; HARREY R. G., TETRAHEDRON LETT. , 1977, NO 24, 2059-2062

  摘要：

  DOI：

文献信息

• Marked Differences in Base Selectivity between DNA and the Free Nucleotides upon Adduct Formation from Bay- and Fjord-Region Diol Epoxides
  作者：SreenivasaRao Vepachedu、Naiqi Ya、Haruhiko Yagi、Jane M. Sayer、Donald M. Jerina

  DOI：10.1021/tx000073w

  日期：2000.9.1

  85% dA adducts on reaction with DNA. With the BaP DEs, 60-77% of the exocyclic amino group adducts formed upon competitive reaction with the free nucleotides are derived from dGMP. The observed dG selectivity of these BaP DEs is much smaller with the nucleotide mixture than it is with DNA, leading to the conclusion that DNA structure has a much larger modifying effect on the base selectivity of the

  由3,4-二羟基-1,2-环氧-1,2,3,4-四氢苯并[c]菲和7,8-二羟基-9,10-的四个旋光异构体中的每一个形成的加合物的分布将环氧，7,8,9,10-四氢苯并[a]（（BcPh和BaP二醇环氧化物）与脱氧腺苷和脱氧鸟苷5'-单磷酸酯的等摩尔混合物反应，与这些二醇环氧化物（DEs）的已知加合物分布进行了比较在体外与小牛胸腺DNA反应后。在dAMP和dGMP的等摩尔混合物（总计100 mM）的存在下，BaP（约40-60％）和BcPh（约30-40％）相对于四醇的所有类型加合物形成效率相当）二醇环氧化合物。这与DNA观察到的四醇和加合物之间的分配不同，其中BcPh DE形成的加合物比BaP DE更有效。对于其中苯甲基羟基和环氧基是反式（DE-2）的DE非对映异构体，dAMP / dGMP混合物中游离核苷酸的环外氨基优先反式与顺式开环。从质上讲，这类似于这些异构体与DNA反应时形成顺
• Covalent nucleoside adducts of benzo[a]pyrene 7,8-diol 9,10-epoxides: structural reinvestigation and characterization of a novel adenosine adduct on the ribose moiety
  作者：Jane M. Sayer、Anju Chadha、Shiv K. Agarwal、Herman J. C. Yeh、Haruhiko Yagi、Donald M. Jerina

  DOI：10.1021/jo00001a007

  日期：1991.1

  The diastereomeric 7,8-diol 9,10-epoxides metabolically derived from the carcinogenic hydrocarbon benzo[alpha]pyrene react with the purine bases in nucleic acids to alkylate their exocyclic amino groups. The major adducts formed from polyguanylic acid and the enantiomers of diol epoxide-1 (the diastereomer in which the benzylic 7-hydroxyl group and the epoxide oxygen are cis) have been shown to result from cis opening of the epoxide by the N-2 amino group of guanine, rather than trans opening as had been previously reported. Four adducts resulting from alkylation of the exocyclic N-6 amino group of adenosine 5'-monophosphate by racemic diol epoxide-1 have been prepared and characterized. In addition, a major adduct formed from adenosine 5'-monophosphate and (-)-(7R,8S)-diol (9R,10S)-epoxide-1, but not from its (+) enantiomer, has been identified as a product of alkylation of the 2'-hydroxyl group of the sugar. We also report a quantitative reevaluation of the extent and distribution of covalent adduct formation from calf thymus DNA and both diastereomeric benzo[alpha]pyrene diol epoxides, as well as the identification of the principal DNA adducts formed from the enantiomers of diol epoxide-1. Tentative identification of several new minor adducts formed upon reaction of diol epoxide-2 with denatured DNA is described. The present results provide additional support for our previously proposed correlation between the signs of the circular dichroism bands of these adducts and their absolute configurations at the N-substituted benzylic carbon atom.
• SAYER, JANE M.;CHADHA, ANJU;AGARWAL, SHIV K.;YEH, HERMAN J. C.;YAGI, HARU+, J. ORG. CHEM., 56,(1991) N, C. 20-29
  作者：SAYER, JANE M.、CHADHA, ANJU、AGARWAL, SHIV K.、YEH, HERMAN J. C.、YAGI, HARU+

  DOI：——

  日期：——
• FU P. P.; HARREY R. G., TETRAHEDRON LETT. <TELE-AY>, 1977, NO 24, 2059-2062
  作者：FU P. P.、 HARREY R. G.

  DOI：——

  日期：——