4-hydroxy-3-[(E)-prop-1-enyl]naphthalene-1,2-dione | 29366-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-3-[(E)-prop-1-enyl]naphthalene-1,2-dione
• 英文别名: 2-hydroxy-3-(prop-1-en-1-yl)naphthalene-1,4-dione；2-hydroxy-3-(prop-1-enyl)-1,4-naphthoquinone；2-hydroxy-3-(2-propenyl)-1,4-naphthoquinone；2-hydroxy-3-propenyl-[1,4]naphthoquinone；lawsone；2-Hydroxy-3-propenyl-[1,4]naphthochinon；2-Hydroxy-3-(prop-1-enyl)-1,4-naphthochinon
• CAS: 29366-41-4
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: SOHLFUWDNFUZAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-[(E)-prop-1-enyl]naphthalene-1,2-dione 在 mercury(II) diacetate 、 盐酸 作用下， 以 溶剂黄146 、 乙醇 为溶剂， 反应 4.0h， 以82%的产率得到2-methylnaphtho[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  发现纳帕布沙星PROTAC作为E3连接酶ZFP91的有效降解剂

  摘要：

  据报道，纳帕布沙星正在接受多项临床试验，可抑制信号转导子和转录因子3（STAT3）。为了更好地阐明其作用机理，我们设计了一种基于纳帕卡辛的针对嵌合体的蛋白水解酶（PROTAC）XD2-149，可抑制胰腺癌细胞系中STAT3信号转导，而不会引起蛋白酶体依赖性STAT3降解。XD2-149的蛋白质组学分析揭示了E3泛素蛋白连接酶ZFP91的下调。XD2-149以纳摩尔范围的DC 50值降解ZFP91 。XD2-149的细胞毒性ZFP91敲低可显着但不完全降低其水平，为其多靶点作用机制提供了证据。NQO1抑制剂双香豆酚可以挽救XD2-149的细胞毒性，但不能挽救ZFP91的降解，这表明NQO1诱导的细胞死亡与ZFP91无关。ZFP91在肿瘤发生中起作用，并参与多种致癌途径，包括NF-κB和HIF-1α。

  DOI：

  10.1021/acs.jmedchem.0c01897
• 作为产物：
  描述：

  2-羟基-3-甲基-1,4-萘醌 在 盐酸 、 sodium hydroxide 、 potassium permanganate 、 溶剂黄146 作用下， 生成 4-hydroxy-3-[(E)-prop-1-enyl]naphthalene-1,2-dione
  参考文献：
  名称：

  On the Oxidation of 2-Hydroxy-1,4-naphthoquinone Derivatives with Alkaline Potassium Permanganate^1,2

  摘要：

  DOI：

  10.1021/ja01298a030

文献信息

• Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation
  作者：Cibelle David、Antonio Lins、Tania Silva、Júlia Campos、Teresinha Silva、Gardenia Militão、Celso Camara

  DOI：10.21577/0103-5053.20180146

  日期：——

  A modified and efficient Knoevenagel condensation procedure was developed to synthesize the title compounds using β-alanine and acetic acid as catalysts, showing good to excellent yields. We used lawsone with suitable aliphatic aldehydes including isobutyraldehyde, 3-methylbutyraldehyde, 2-ethylbutyraldehyde, phenylacetaldehyde, 2-phenyl-propionaldehyde, among others. These compounds were submitted

  开发了一种改进的有效的Knoevenagel缩合方法，以β-丙氨酸和乙酸为催化剂合成标题化合物，显示出良好或优异的收率。我们使用了具有适当脂族醛的Lawsone，其中脂族醛包括异丁醛，3-甲基丁醛，2-乙基丁醛，苯基乙醛，2-苯基丙醛等。这些化合物针对三种肿瘤细胞系进行了细胞毒性筛选，这些肿瘤细胞系表现出良好至优异的细胞毒性谱。
• Chemistry of naphthazarin derivatives 13. Conformational analysis of 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones by quantum chemistry methods
  作者：V. P. Glazunov、D. V. Berdyshev、A. Ya. Yakubovskaya、N. D. Pokhilo

  DOI：10.1007/s11172-006-0480-z

  日期：2006.10

  The molecular structures of various conformers of 2-hydroxy-1,4-naphthoquinone; 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones; 2,5,8-trihydroxy-1,4-naphthoquinone; and 3-(alk-1-enyl)-2,5,8-trihydroxy-1,4-naphthoquinones were studied by density functional theory (B3LYP/6-31(d), B3LYP/6-31(d, p)) and ab initio (MP2/6-31G, MP2/6-31(d)) methods. The strengths of the intramolecular hydrogen bonds formed by the β-hydroxy group with the O atom at C(1) and with the double bond π-electrons of the alkenyl substituents in the quinonoid rings were estimated. The compounds studied mainly exist as rotamers with the former-type hydrogen bonds. The splitting of the quinonoid bands of the stretching vibrations of the β-hydroxy group in the IR spectra of 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones and 3-(alk-1-enyl)-2,5,8-trihydroxy-1,4-naphthoquinones in hexane solutions is due to the existence of rotamers formed upon internal rotation of the alkenyl substituent.

  通过密度泛函理论 (B3LYP/6-31(d), B3LYP/6-31(d, p)) 和从头算 (MP2/6-31G, MP2/6-31(d)) 方法研究了2-羟基-1,4-萘醌、3-(链烯-1-基)-2-羟基-1,4-萘醌、2,5,8-三羟基-1,4-萘醌和3-(链烯-1-基)-2,5,8-三羟基-1,4-萘醌的各种构象分子的分子结构。估算了β-羟基与C(1)位氧原子及与醌环上链烯基取代基双键π电子形成的分子内氢键的强度。所研究的化合物主要以形成前一种类型氢键的旋转异构体形式存在。3-(链烯-1-基)-2-羟基-1,4-萘醌和3-(链烯-1-基)-2,5,8-三羟基-1,4-萘醌在己烷溶液中的红外光谱中β-羟基伸缩振动的醌带分裂是由于链烯基取代基内旋转形成的旋转异构体存在所致。
• A Complete and Unambiguous 1H and 13C NMR Signals Assignment of para- Naphthoquinones, ortho- and para-Furanonaphthoquinones
  作者：Tatiane Borgati、José de Souza、Alaíde de Oliveira

  DOI：10.21577/0103-5053.20190009

  日期：——

  A complete and unambiguous assignment of H and C nuclear magnetic resonance (NMR) signals of 29 naphthoquinones is reported on the basis of oneand two-dimensional NMR techniques (H, C, H-H correlated spectroscopy (COSY) and H-C heteronuclear multiple-bond correlation (HMBC)). This is the first report distinguishing data between para-naphthoquinones, orthoand para-furanonaphthoquinones isomers.

  基于一维和二维NMR技术（H，C，HH相关光谱（COSY）和HC异核多键相关（ HMBC））。这是第一份区分对萘醌，邻和对呋喃萘甲醌异构体的数据的报告。
• Antitumor agents. 89. Psychorubrin, a new cytotoxic naphthoquinone from Psychotria rubra and its structure-activity relationships
  作者：Toshimitsu Hayashi、Forrest T. Smith、Kuo Hsiung Lee

  DOI：10.1021/jm00394a013

  日期：1987.11

  A new naphthoquinone, isolated from the alcoholic extract of Psychotria rubra, exhibited significant cytotoxicity in the KB cell assay (ED50 = 3.0 micrograms/mL). Spectral data was used to assign the structure of psychorubrin as 2. Naphthoquinone derivatives 6, 8, 13, and 14 were prepared and exhibited superior cytotoxic activity to that of psychorubrin. All were potential Michael acceptors whose conjugation

  从Psychotria rubra的酒精提取物中分离出的新萘醌在KB细胞测定中表现出显着的细胞毒性（ED50 = 3.0微克/ mL）。光谱数据被用于将精神尿蛋白的结构指定为2。制备了萘醌衍生物6、8、13和14，并表现出比精神尿蛋白更好的细胞毒活性。所有这些都是潜在的迈克尔受体，其结合已扩展。然而，当此类化合物中存在亲水性羟基时，观察到体外活性降低。
• Ortho-quinone derivatives novel synthesis therefor and their use in the
  申请人：Wisconsin Alumni Research Foundation

  公开号：US05824700A1

  公开（公告）日：1998-10-20

  The invention relates to .beta.-lapachone derivatives of formula II and compositions containing said compounds: ##STR1## wherein, R.sup.5, R.sup.6 and R.sup.7 are as defined in the specification. The compounds are potent inhibitors of neoplastic cell growth and proliferation.

  本发明涉及公式II的β-萝芦醌衍生物及含有该化合物的组合物：##STR1## 其中，R.sup.5、R.sup.6和R.sup.7如规范中所定义。该化合物是肿瘤细胞生长和增殖的强效抑制剂。