3-isopropyl-[1,2]naphthoquinone | 133130-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-isopropyl-[1,2]naphthoquinone
• 英文别名: 3-Isopropyl-[1,2]naphthochinon；3-Isopropylnaphthalene-1,2-dione；3-propan-2-ylnaphthalene-1,2-dione
• CAS: 133130-13-9
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: KGCDZSGUSQQVKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  3-isopropyl-[1,2]naphthoquinone 、 4-乙酰氨基苯硫酚 以 甲醇 、 氯仿 为溶剂， 生成 N-[4-(2-Isopropyl-3,4-dioxo-3,4-dihydro-naphthalen-1-ylsulfanyl)-phenyl]-acetamide
  参考文献：
  名称：

  Synthesis of miltirone analogues as inhibitors of Cdc25 phosphatases

  摘要：

  Miltirone analogues were synthesized and evaluated for inhibitory activity against Cdc25 and PTP1B. Most of the compounds demonstrated potent Cdc25 inhibitory activity, and several exhibited higher selectivity for Cdc25 than for PTP1B. In a cytotoxic assay, most of the compounds displayed cytotoxicity against the tumor cell lines A549 and HCT-116, producing IC50 values in the micromolar range. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.080
• 作为产物：
  描述：

  4-hydroxy-3-propan-2-ylnaphthalene-1,2-dione 在 盐酸 、 amalgamated zinc 作用下， 生成 3-isopropyl-[1,2]naphthoquinone
  参考文献：
  名称：

  Rearrangement and Reduction of Hindered 2-Hydroxy-3-alkyl-1,4-naphthoquinones

  摘要：

  DOI：

  10.1021/ja01146a052

文献信息

• Compounds from Danshen. Part 4. Structure-activity relationship of miltirone, an active central benzodiazepine receptor ligand isolated from Salvia miltiorrhiza Bunge (Danshen)
  作者：Hson Mou Chang、Kuk Ying Chui、Fan Wah Lau Tan、Yun Yang、Zeng Pei Zhong、Chi Ming Lee、Hing Leung Sham、Henry N. C. Wong

  DOI：10.1021/jm00109a022

  日期：1991.5

  Twenty one o-quinonoid-type compounds and one coumarin-type compound related to miltirone (1) have been synthesized with the aim to identify the key structural elements involved in miltirone's interaction with the central benzodiazepine receptor. On the basis of their inhibition of [H-3]flunitrazepam binding to bovine cerebral cortex membranes, it is apparent that ring A of miltirone is essential for affinity. Although increasing the size of ring A from six-membered to seven- and eight-membered is well-tolerated, the introduction of polar hydroxyl groups greatly reduces binding affinity. The presence of 1,1-dimethyl groups on ring A is, however, not essential. On the other hand, the isopropyl group on ring C appears to be critical for binding as its removal decreases affinity by more than 30-fold. It can, however, be replaced with a methyl group with minimal reduction in affinity. Finally, linking ring A and B with a -CH2CH2- bridge results in analogue 89, which is 6 times more potent than miltirone at the central benzodiazepine receptor (IC50 = 0.05-mu-M).
• CHANG, HSON MOU;CHUI, KUK YING;TAN, FAN WAH LAU;YANG, YUN;ZHONG, ZENG PEI+, J. MED. CHEM., 34,(1991) N, C. 1675-1692
  作者：CHANG, HSON MOU、CHUI, KUK YING、TAN, FAN WAH LAU、YANG, YUN、ZHONG, ZENG PEI+

  DOI：——

  日期：——