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4-Nitroestratriene-3,17beta-diol | 6936-94-3

中文名称
——
中文别名
——
英文名称
4-Nitroestratriene-3,17beta-diol
英文别名
13-methyl-2-nitro-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3,17-diol;4-nitro-17β-estradiol;4-nitroestradiol;2-nitroestradiol;4-nitro-estratriene-(1.3.5(10))-diol-(3.17β);(8R)-4-Nitro-3.17c-dihydroxy-13c-methyl-(8rH.9tH.14tH)-7.8.9.11.12.13.14.15.16.17-decahydro-6H-cyclopenta[a]phenanthren;4-Nitroestra-1,3,5(10)-triene-3,17beta-diol;(8R,9S,13S,14S,17S)-13-methyl-4-nitro-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
4-Nitroestratriene-3,17beta-diol化学式
CAS
6936-94-3
化学式
C18H23NO4
mdl
——
分子量
317.385
InChiKey
OMZSNIQSXZEIKB-ZHIYBZGJSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.4
  • 重原子数:
    23
  • 可旋转键数:
    0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.67
  • 拓扑面积:
    86.3
  • 氢给体数:
    2
  • 氢受体数:
    4

SDS

SDS:00ff72cb208bbd9082211ff31659a997
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    4-Nitroestratriene-3,17beta-diol 在 horseradish peroxidase EC 1.11.1.7 phosphate buffer 、 亚硝酸钠-15N双氧水 作用下, 以 甲醇 为溶剂, 生成
    参考文献:
    名称:
    17β-Estradiol nitration by peroxidase/H2O2/NO2−: a chemical assessment
    摘要:
    Nitration of 17beta-estradiol by H2O2 and nitrite in the presence of various peroxidases, viz. horseradish peroxidase, lactoperoxidase, and peroxidase-containing homogenates from bovine uteri, was systematically investigated to assess on a chemical basis its potential relevance to the mechanisms of impairment of estrogen functions under oxidative/nitrosative stress conditions. In the presence of excess nitrite 17beta-estradiol reacted smoothly to give 2-nitroestradiol (1), 4-nitroestradiol (2), and 2,4-dinitroestradiol (3). With 10-300 muM estradiol, formation yields of 1-3 were 12-55%, but dropped to 1% or less at lower estrogen concentration, for example, 1 muM, or in plasma as the reaction medium. Time course analysis showed that 2 is the prevalent nitration product under conditions of slow generation of nitrating species, suggesting some regioselectivity for estradiol nitration at C-4, whereas 1 prevails with bolus addition of reagents, due to faster degradation of 2. Competition experiments carried out with (NO2-)-N-15 showed that 2 is about twice more susceptible to nitration than 1 as determined by N-15 NMR analysis of the resulting 3. The biological effects of 1 and 2 were preliminarily tested on in vitro bovine embryo cultures. When 1 and 2 were substituted to the standard 17beta-estradiol in the oocyte maturation, a significant decrease in both cleavage and blastocyst efficiency was observed in the case of 1 but not 2. Overall, these results suggest that estradiol nitration is a potential pathway of hormonal dysfunction and toxicity but would require elevated estrogen levels of questionable physiological relevance. (C) 2004 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2004.03.036
  • 作为产物:
    描述:
    雌二醇 在 bismuth nitrate pentahydrate montmorillonite KSF clay 作用下, 以 二氯甲烷 为溶剂, 以75%的产率得到4-Nitroestratriene-3,17beta-diol
    参考文献:
    名称:
    Bismuth nitrate-induced novel nitration of estradiol: An entry to new anticancer agents
    摘要:
    Direct nitration of estradiol was carried out using metal nitrates on solid surfaces under mild condition, and a combination of bismuth nitrate pentahydrate impregnated KSF clay was found to be the best reagent to synthesize 2- and 4-nitroestradiol effectively. Furthermore, various basic side chains were introduced, through O-linker at C-3, to these nitroestradiols. The ability of these derivatives to cause cytotoxicity in Estrogen Receptor (ER)-positive and ER-negative breast cancer cell lines, as well as cancer cell lines of other origins, was examined. Qualitative structure activity relationship (SAR) has also been studied. We found that a basic side chain containing either a piperidine or morpholine ring, when conjugated to 2-nitroestradiol, was particularly effective at causing cytotoxicity in each of the cancer cell lines examined. Surprisingly, this effective cytotoxicity was even seen in ER-negative breast cancer cells. (C) 2014 Elsevier Masson SAS. All rights reserved.
    DOI:
    10.1016/j.ejmech.2014.06.010
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文献信息

  • Oxidative chemistry of 2-nitro and 4-nitroestradiol: Dichotomous behavior of radical intermediates and novel potential routes for oxyfunctionalization and B-ring fission of steroidal scaffolds
    作者:A PEZZELLA、P MANINI、A NAPOLITANO、O CRESCENZI、V BARONE、M DISCHIA
    DOI:10.1016/j.steroids.2005.01.006
    日期:2005.7
    9(11)-tetraene-3,12,17-triol (6). With higher concentrations of H(2)O(2), the novel secoestra-1(10),2,4-trien-9-one derivative 7 was obtained from 2. Theoretical calculations suggested that the peculiar behavior of 2 may be due to the generation of a relatively stable radical intermediate at C(9), which would then be converted to the reactive quinone methide 8. The chemistry described in this paper appears to be
    过氧化物酶/ H(2)O(2)系统氧化4-硝基-17β-雌二醇(1)通过苯氧基自由基偶联得到对称的C(2)-连接的二聚体(3)。2-硝基17β-雌二醇(2)的相似氧化反应(其中硝基与芳环共面)产生9α-和9β-羟基-2-硝基-17β-雌二醇(4a,b)(17beta) -2-nitroestra-1(10),2,4,9(11)-丁烯-3,17-二醇(5)和(12alpha,17beta)-2-nitroestra-1(10),2,4, 9(11)-四烯-3,12,17-三醇(6)。随着更高浓度的H(2)O(2),新型secoestra-1(10),2,4-trien-9-one衍生物7从2获得。理论计算表明2的特殊行为可能是由于会在C(9)处生成相对稳定的自由基中间体,然后将其转化为反应性醌甲基化物8。
  • Convenient large scale preparation of catechol estrogens
    作者:G. Stubenrauch、R. Knuppen
    DOI:10.1016/0039-128x(76)90010-6
    日期:1976.11
    2-Hydroxyestrone, 2-hydroxyestradiol-17beta, 2-hydroxy-17alpha-ethynylestradiol, 2-hydroxyestriol, 4-hydroxyestrone, 4-hydroxyestradiol-17beta, 4-hydroxy-17alpha-ethynylestradiol and 4-hydroxyestriol are prepared on a preparative scale from the corresponding aminophenols using a new inverse oxidation procedure. By the synthesis described both the 2- and 4-hydroxylated estrogens are available in high yields.
  • Darstellung biochemisch interessanter Thioäther der Östrogene, II. 2-Methoxy-4-carboxymethylmercapto-östron-3-methyläther
    作者:FRIEDRICH MARKS、ELLEN KUBINYI、ERICH HECKER
    DOI:10.1515/bchm2.1968.349.2.1215
    日期:1968.1
  • Nitrated estrogenic hormones
    申请人:NIEDERL JOSEPH B
    公开号:US02438819A1
    公开(公告)日:1948-03-30
  • Notes: Synthesis of Nitroestradiols
    作者:Tad Patton
    DOI:10.1021/jo01093a611
    日期:1959.11
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同类化合物

(5β)-17,20:20,21-双[亚甲基双(氧基)]孕烷-3-酮 (5α)-2′H-雄甾-2-烯并[3,2-c]吡唑-17-酮 (3β,20S)-4,4,20-三甲基-21-[[[三(异丙基)甲硅烷基]氧基]-孕烷-5-烯-3-醇-d6 (25S)-δ7-大发酸 (20R)-孕烯-4-烯-3,17,20-三醇 (11β,17β)-11-[4-({5-[(4,4,5,5,5-五氟戊基)磺酰基]戊基}氧基)苯基]雌二醇-1,3,5(10)-三烯-3,17-二醇 齐墩果酸衍生物1 黄麻属甙 黄芪皂苷III 黄芪皂苷 II 黄芪甲苷 IV 黄芪甲苷 黄肉楠碱 黄果茄甾醇 黄杨醇碱E 黄姜A 黄夹苷B 黄夹苷 黄夹次甙乙 黄夹次甙乙 黄夹次甙丙 黄体酮环20-(乙烯缩醛) 黄体酮杂质EPL 黄体酮杂质1 黄体酮杂质 黄体酮杂质 黄体酮EP杂质M 黄体酮EP杂质G(RRT≈2.53) 黄体酮EP杂质F 黄体酮6-半琥珀酸酯 黄体酮 17alpha-氢过氧化物 黄体酮 11-半琥珀酸酯 黄体酮 麦角甾醇葡萄糖苷 麦角甾醇氢琥珀酸盐 麦角甾烷-6-酮,2,3-环氧-22,23-二羟基-,(2b,3b,5a,22R,23R,24S)-(9CI) 麦角甾烷-3,6,8,15,16-五唑,28-[[2-O-(2,4-二-O-甲基-b-D-吡喃木糖基)-a-L-呋喃阿拉伯糖基]氧代]-,(3b,5a,6a,15b,16b,24x)-(9CI) 麦角甾烷-26-酸,5,6:24,25-二环氧-14,17,22-三羟基-1-羰基-,d-内酯,(5b,6b,14b,17a,22R,24S,25S)-(9CI) 麦角甾-8-烯-3-醇 麦角甾-8,24(28)-二烯-26-酸,7-羟基-4-甲基-3,11-二羰基-,(4a,5a,7b,25S)- 麦角甾-7,22-二烯-3-酮 麦角甾-7,22-二烯-17-醇-3-酮 麦角甾-5,24-二烯-26-酸,3-(b-D-吡喃葡萄糖氧基)-1,22,27-三羟基-,d-内酯,(1a,3b,22R)- 麦角甾-5,22,25-三烯-3-醇 麦角甾-4,6,8(14),22-四烯-3-酮 麦角甾-1,4-二烯-3-酮,7,24-二(乙酰氧基)-17,22-环氧-16,25-二羟基-,(7a,16b,22R)-(9CI) 麦角固醇 麦冬皂苷D 麦冬皂苷D 麦冬皂苷 B