7-羟基-4-异丙基-色烯-2-酮 | 23251-28-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 7-羟基-4-异丙基-色烯-2-酮
• 英文名称: 7-hydroxy-4-isopropylcoumarin
• 英文别名: 7-Hydroxy-4-isopropyl-chromen-2-one；7-hydroxy-4-propan-2-ylchromen-2-one
• CAS: 23251-28-7
• 化学式: C₁₂H₁₂O₃
• mdl: MFCD04612954
• 分子量: 204.225
• InChiKey: ZPZNGNXYGLIIKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  7-羟基-4-异丙基-色烯-2-酮 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)butoxy)-4-isopropyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and Biological Investigation of Coumarin Piperazine (Piperidine) Derivatives as Potential Multireceptor Atypical Antipsychotics

  摘要：

  The discovery and synthesis of potential and novel antipsychotic coumarin derivatives, associated with potent dopamine 132, D3, and serotonin S-HT1A and S-HT2A, receptor properties, are the focus of the present article. The most-promising derivative was 7-(4-(4-(6-fluorobenzo[d]-isoxazol-3-yl)-piperidin-1-yl)butoxy)-4-methyl-8-chloro-2H- chromen-2-one (17m). This derivative possesses unique pharmacological features, including high affinity for dopamine D-2 and D-3 and serotonin S-HT1A and 5-HT2A receptors. Moreover, it possesses low affinity for S-HT2C and H-1 receptors (to reduce the risk of obesity associated with chronic treatment) and hERG channels (to reduce the incidence of torsade des pointes). In animal models, compound 17m inhibited apomorphine-induced climbing behavior, MK-801-induced hyperactivity, and the conditioned avoidance response without observable catalepsy at the highest dose tested. Further, fewer preclinical adverse events were noted with 17m compared with risperidone in assays that measured prolactin secretion and weight gain. Acceptable pharmacokinetic properties were also noted with 17m. Taken together, 17m may constitute a novel class of drugs for the treatment of schizophrenia.

  DOI：

  10.1021/jm400408r
• 作为产物：
  描述：

  3-甲基-2-丁酮 在 甲烷磺酸 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 6.58h， 生成 7-羟基-4-异丙基-色烯-2-酮
  参考文献：
  名称：

  发现一种新型、有效、口服活性且安全的靶向人线粒体 RNA 聚合酶的抑制剂

  摘要：

  高氧化磷酸化 (OXPHOS) 发生在一些肿瘤中，这依赖于 OXPHOS 的能量供应，特别是在慢循环肿瘤细胞中。因此，靶向人线粒体 RNA 聚合酶 (POLRMT) 以抑制线粒体基因表达成为根除肿瘤细胞的潜在治疗策略。在这项工作中，对一流的 POLRMT 抑制剂 IMT1B 及其 SAR 的探索和优化导致鉴定出一种新型化合物D26，该化合物对多种癌细胞具有强烈的抗增殖作用，并降低线粒体相关基因的表达。此外，机制研究表明D26在 G1 期阻止细胞周期，对 A2780 细胞的细胞凋亡、去极化线粒体或反应性氧化应激的产生没有影响。重要的是，D26在 A2780 异种移植裸鼠中表现出比先导 IMT1B 更有效的抗癌活性，并且没有可观察到的毒性作用。所有结果表明，D26作为一种有效且安全的抗肿瘤候选物值得进一步研究。

  DOI：

  10.1021/acs.jmedchem.3c00058

文献信息

• Anti-AIDS Agents. 37. Synthesis and Structure−Activity Relationships of (3‘<i>R</i>,4‘<i>R</i>)-(+)-<i>cis</i>-Khellactone Derivatives as Novel Potent Anti-HIV Agents
  作者：Lan Xie、Yasuo Takeuchi、L. Mark Cosentino、Kuo-Hsiung Lee

  DOI：10.1021/jm9900624

  日期：1999.7.1

  (+)-cis-khellactone derivatives as novel anti-HIV agents, 24 monosubstituted 3', 4'-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) derivatives were synthesized asymmetrically. These compounds included 4 isomeric monomethoxy analogues (3-6), 4 isomeric monomethyl analogues (7-10), 4 4-alkyl/aryl-substituted analogues (11-14), and 12 4-methyl-(+)-cis-khellactone derivatives (15-26) with varying 3', 4'-substituents

  为了探索作为新型抗HIV药物的（+）-顺式-khellactone衍生物的结构要求，使用24个单取代的3'，4'-di-O-（S）-樟脑酰基-（+）-顺式-khellactone（DCK）衍生物不对称合成。这些化合物包括4个异构的单甲氧基类似物（3-6），4个异构的单甲基类似物（7-10），4个4-烷基/芳基取代的类似物（11-14）和12个4-甲基-（+）-顺式具有3'，4'取代基的khellactone衍生物（15-26）。这些（+）-顺式-khellactone衍生物被筛选针对急性感染的H9淋巴细胞中的HIV-1复制。结果表明，（3'R，4'R）-（+）-顺式-khellactone骨架，3'-和4'-位置的两个（S）-（-）-樟脑酰基和甲基除6-位以外，香豆素环上的α是抗HIV活性的最佳结构部分。3-甲基-（7），4-甲基-（8）和5-甲基-（9）3'，4'-二-O-（S）-樟脑酰基-（3'R，4'R）-
• Ito, Kiichi; Nakajima, Kaoru, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 511 - 515
  作者：Ito, Kiichi、Nakajima, Kaoru

  DOI：——

  日期：——
• Dihydroxylation of Functionalized Coumarin Derivatives
  作者：Takuya Kumamoto、Tsutomu Ishikawa、Keiko Fusegi、Waka Nakanishi

  DOI：10.3987/com-08-s(f)29

  日期：——

  7-Acetoxy- and 7-tosyloxycoumarins were successfully dihydroxylated in RuCl3/NaIO4/CeCl3 system to give the corresponding glycol derivatives in excellent yields. Tricyclic coumarin with tetrasubstituted olefin function also gave the desired diol in good yield. Introduction of electron-deficient protecting group to coumarin skeleton is critical for the successful dihydroxylation.
• ITO, KIICHI;NAKAJIMA, KAORU, J. HETEROCYCL. CHEM., 25,(1988) N 2, 511-515
  作者：ITO, KIICHI、NAKAJIMA, KAORU

  DOI：——

  日期：——
• [EN] RESORCINOL DERIVATIVES FOR THEIR COSMETIC USE<br/>[FR] UTILISATION COSMÉTIQUE DES DÉRIVÉS DU RÉSORCINOL
  申请人：OREAL

  公开号：WO2017102802A1

  公开（公告）日：2017-06-22

  The present invention relates to a compound of formula (I) for its depigmenting, lightening and/or bleaching the skin in which R1 and R2 independently denote H, an alkyl radical, a radical S* denoting a monosaccharide sugar radical or a polysaccharide sugar radical, a radical COR6; R3 denotes a C1-C20 alkyl radical; R4 and R5 independently denote H, a saturated C1-C20 or unsaturated C2-C20 or branched C3-C20, or cyclic C3-C8 alkyl radical, which is optionally interrupted and/or optionally substituted; R7 and R8, which may be identical or different, being chosen from H, an unsaturated linear C1-C10 alkyl group, an unsaturated linear C2-C10 alkyl group, a saturated or unsaturated branched C3-C10 alkyl group, and a C3-C8 cycloalkyl group; a (C1-C4)alkyl(hetero)(C6)aryl group optionally containing a nitrogen atom, especially a benzyl group; an acetyl radical, and also the salts thereof, the solvates thereof and the optical and/or geometrical isomers thereof, and the racemic mixtures thereof, alone or as a mixture. The present invention also relates to novel compounds (II), and also to the process for preparing them and to a cosmetic process for depigmenting the skin using such compounds (I) or (II).