3,4-dihydro-5-methoxy-6-nitro-1(2H)-naphthalenone | 192576-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-dihydro-5-methoxy-6-nitro-1(2H)-naphthalenone
• 英文别名: 5-methoxy-6-nitro-1-tetralone；5-methoxy-6-nitro-3,4-dihydro-2H-naphthalen-1-one
• CAS: 192576-52-6
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: JQFWYIAVPOXTKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-5-methoxy-6-nitro-1(2H)-naphthalenone 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 生成 6-amino-5-methoxy-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  环A和F修饰的六环喜树碱类似物的合成及其抗肿瘤活性。

  摘要：

  通过适当取代的双环氨基酮与三环酮的弗里德兰德缩合合成喜树碱的19个A和F环修饰的六环类似物，并评价其细胞毒性和拓扑异构酶I抑制活性。17种化合物对小鼠白血病P388和人肿瘤细胞系HOC-21和QG-56的细胞毒性作用与7-乙基-10-羟基喜树碱（SN-38）相当或更好。在六环化合物的A环的5位上引入致密且感应吸电子的取代基，例如羟基，甲氧基，氯或氟基，显着提高了抗肿瘤活性。拓扑异构酶I抑制这些化合物的效力与其细胞毒性显示出良好的相关性。他们之中，

  DOI：

  10.1021/jm970765q
• 作为产物：
  描述：

  5-甲氧基-3,4-二氢-2H-1-萘酮 在 乙酸酐 作用下， 以 乙醚 为溶剂， 以46%的产率得到3,4-dihydro-5-methoxy-6-nitro-1(2H)-naphthalenone
  参考文献：
  名称：

  Conformationally constrained analogues of N′-(4-tert-butylbenzyl)-N-(4-methylsulfonylaminobenzyl)thiourea as TRPV1 antagonists

  摘要：

  A series of bicyclic analogues having indan and tetrahydronaphthalene templates in the A-region were designed as conformationally constrained analogues of our previously reported potent TRPV1 antagonists (1, 3). The activities for rat TRPV1 of the conformationally restricted analogues were moderately or markedly diminished, particularly in the case of the tetrahydronaphthalene analogues. The analysis indicated that steric constraints at the benzylic position in the bicyclic analogues may be an important factor for their unfavorable interaction with the receptor. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.026

文献信息

• Synthesis and Antitumor Activity of Ring A- and F-Modified Hexacyclic Camptothecin Analogues
  作者：Masamichi Sugimori、Akio Ejima、Satoru Ohsuki、Kouichi Uoto、Ikuo Mitsui、Yasuyoshi Kawato、Yasuhide Hirota、Keiki Sato、Hirofumi Terasawa

  DOI：10.1021/jm970765q

  日期：1998.6.1

  and F-modified hexacyclic analogues of camptothecin were synthesized by Friedlander condensation of appropriately substituted bicyclic amino ketones with tricyclic ketone and were evaluated for cytotoxicity and topoisomerase I inhibitory activity. Seventeen of the compounds showed cytotoxic effects comparable or superior to those of 7-ethyl-10-hydroxycamptothecin (SN-38) against mouse leukemia P388 and

  通过适当取代的双环氨基酮与三环酮的弗里德兰德缩合合成喜树碱的19个A和F环修饰的六环类似物，并评价其细胞毒性和拓扑异构酶I抑制活性。17种化合物对小鼠白血病P388和人肿瘤细胞系HOC-21和QG-56的细胞毒性作用与7-乙基-10-羟基喜树碱（SN-38）相当或更好。在六环化合物的A环的5位上引入致密且感应吸电子的取代基，例如羟基，甲氧基，氯或氟基，显着提高了抗肿瘤活性。拓扑异构酶I抑制这些化合物的效力与其细胞毒性显示出良好的相关性。他们之中，
• Pinna; Loriga; Curzu, Il Farmaco, 1997, vol. 52, # 1, p. 25 - 28
  作者：Pinna、Loriga、Curzu、D'Amico

  DOI：——

  日期：——
• Conversion of Enediynes into Quinones by Antibody Catalysis and in Aqueous Buffers:  Implications for an Alternative Enediyne Therapeutic Mechanism
  作者：Lyn H. Jones、Curtis W. Harwig、Paul Wentworth、Anton Simeonov、Anita D. Wentworth、Sandrine Py、Jon A. Ashley、Richard A. Lerner、Kim D. Janda

  DOI：10.1021/ja005864z

  日期：2001.4.1
• Conformationally constrained analogues of N′-(4-tert-butylbenzyl)-N-(4-methylsulfonylaminobenzyl)thiourea as TRPV1 antagonists
  作者：Ju-Ok Lim、Mi-Kyoung Jin、HyungChul Ryu、Dong Wook Kang、Jeewoo Lee、Larry V. Pearce、Richard Tran、Attila Toth、Peter M. Blumberg

  DOI：10.1016/j.ejmech.2008.02.026

  日期：2009.1

  A series of bicyclic analogues having indan and tetrahydronaphthalene templates in the A-region were designed as conformationally constrained analogues of our previously reported potent TRPV1 antagonists (1, 3). The activities for rat TRPV1 of the conformationally restricted analogues were moderately or markedly diminished, particularly in the case of the tetrahydronaphthalene analogues. The analysis indicated that steric constraints at the benzylic position in the bicyclic analogues may be an important factor for their unfavorable interaction with the receptor. (C) 2008 Elsevier Masson SAS. All rights reserved.