4-hydroxy-3-[(1-hydroxy-3,4-dioxonaphthalen-2-yl)methyl]naphthalene-1,2-dione | 4195-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-3-[(1-hydroxy-3,4-dioxonaphthalen-2-yl)methyl]naphthalene-1,2-dione
• 英文别名: 3,3′-methylenebis(2-hydroxynaphthalene-1,4-dione)；2,2′-methylenebis(3-hydroxynaphthoquinone)；2,2'-methylenebis(3-hydroxy-1,4-naphthoquinone)；methylene-3,3'-bilawsone；diphthiocol；3,3'-dihydroxy-2,2'-methanediyl-di-[1,4]naphthoquinone；3,3'-Dihydroxy-2,2'-methandiyl-di-[1,4]naphthochinon
• CAS: 4195-02-2
• 化学式: C₂₁H₁₂O₆
• 分子量: 360.323
• InChiKey: IZSITCOQYPAKPE-UHFFFAOYSA-N

物化性质

• 熔点：
  249-251 °C (decomp)
• 沸点：
  601.6±55.0 °C(Predicted)
• 密度：
  1.603±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  108.74
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-[(1-hydroxy-3,4-dioxonaphthalen-2-yl)methyl]naphthalene-1,2-dione 、 乙酸酐 在 硫酸 作用下， 生成 3,3'-diacetoxy-2,2'-methanediyl-di-[1,4]naphthoquinone
  参考文献：
  名称：

  Synthesis of Potential Anticancer Agents. IX. Lawsone Derivatives Containing an Alkylating Function^1,2

  摘要：

  DOI：

  10.1021/jo01351a059
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 甲醇 、 碘甲烷 作用下， 生成 4-hydroxy-3-[(1-hydroxy-3,4-dioxonaphthalen-2-yl)methyl]naphthalene-1,2-dione
  参考文献：
  名称：

  Naphthoquinone Antimalarials. Mannich Bases Derived from Lawsone

  摘要：

  DOI：

  10.1021/ja01173a042

文献信息

• A New Method for Thiomethylation of Hydroxy-1,4-naphthoquinones with N-Acetyl-l-cysteine; First Synthesis of Fibrostatins B, C, and D
  作者：Sergey Polonik、Yuri Sabutskii、Vladimir Denisenko、Pavel Dmitrenok

  DOI：10.1055/s-0034-1378522

  日期：——

  4-dioxo-1,4-dihydronaphthalen-2-yl)methyl]-l-cysteine conjugates were obtained in good yields by acid-catalyzed condensation of substituted 2-hydroxy-1,4-naphthoquinones with N-acetyl-l-cysteine and paraform­aldehyde. Based on this reaction, a first synthesis of fibrostatins B, C, and D was developed. A series of N-acetyl-S-[(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl]-l-cysteine conjugates were

  摘要 通过酸催化取代基的缩合反应，可以得到高收率的一系列N-乙酰基-S -[（3-羟基-1,4-二氧杂-1,4-二氢萘-2-基）甲基] -1-半胱氨酸结合物。 2-羟基-1，4-萘醌与N-乙酰基-1-半胱氨酸和多聚甲醛。基于该反应，开发了纤维抑素B，C和D的第一合成。 通过酸催化取代基的缩合反应，可以得到高收率的一系列N-乙酰基-S -[（3-羟基-1,4-二氧杂-1,4-二氢萘-2-基）甲基] -1-半胱氨酸结合物。 2-羟基-1，4-萘醌与N-乙酰基-1-半胱氨酸和多聚甲醛。基于该反应，开发了纤维抑素B，C和D的第一合成。
• (3,3’-Methylene)bis-2-hydroxy-1,4-naphthoquinones induce cytotoxicity against DU145 and PC3 cancer cells by inhibiting cell viability and promoting cell cycle arrest
  作者：Paula Priscilla de Freitas、Ruan Carlos Busquet Ribeiro、Isabella dos Santos Guimarães、Caroline S. Moreira、David R. Rocha、Fernando de Carvalho da Silva、Vitor Francisco Ferreira、Etel Rodrigues Pereira Gimba

  DOI：10.1007/s11033-021-06406-w

  日期：2021.4

  We developed a novel method for the synthesis of bis-naphthoquinones (BNQ), which are hybrids of lawsone (2-hydroxy-1,4-naphthoquinone) and 3-hydroxy-juglone (3,5-dihydroxy-1,4-naphthoquinone). The anticancer activity of three synthesized compounds, named 4 (RC10), 5 (RCDFC), and 6 (RCDOH) was evaluated in vitro against two metastatic prostate cancer (PCa) cell lines, DU145 and PC3, using MTT assays. We found that 4 (RC10) and 5 (RCDFC) induced cytotoxicity against DU145 and PC3 cells. Flow cytometry analysis revealed that these two compounds promoted cell cycle arrest in G1/S and G2/M phases, increased Sub-G1 peak and induced inhibition in cell viability. We also showed that these effects are cell-type context dependent and more selective for these tested PCa cells than for HUVEC non-tumor cells. The two BNQ compounds 4 (RC10) and 5 (RCDFC) displayed promising anticancer activity against the two tested metastatic PCa cell lines, DU145 and PC3. Their effects are mainly associated with inhibition of cell viability, possibly through apoptotic cell death, besides altering the SubG1, G1/S and G2/M phases of cell cycle. 5 (RCDFC) compound was found to be more selective than 4 (RC10), when comparing their cytotoxic effects in relation to HUVEC non-tumoral cells. Future work should also test these compounds in combination with other chemotherapeutic drugs to evaluate their effects on further sensitizing drug-resistant metastatic PCa cells.

  我们开发了一种合成双萘醌（BNQ）的新方法，双萘醌是 lawsone（2-羟基-1,4-萘醌）和 3-hydroxy-juglone （3,5-二羟基-1,4-萘醌）的混合物。我们利用 MTT 试验，在体外评估了名为 4 (RC10)、5 (RCDFC) 和 6 (RCDOH) 的三种合成化合物对两种转移性前列腺癌（PCa）细胞系 DU145 和 PC3 的抗癌活性。我们发现 4（RC10）和 5（RCDFC）对 DU145 和 PC3 细胞具有细胞毒性。流式细胞术分析表明，这两种化合物能促进细胞周期停滞在 G1/S 和 G2/M 期，增加 Sub-G1 峰值，并抑制细胞活力。我们还发现，这些效应与细胞类型有关，而且与 HUVEC 非肿瘤细胞相比，它们对 PCa 细胞的选择性更强。两种 BNQ 化合物 4（RC10）和 5（RCDFC）对两种受测的转移性 PCa 细胞系（DU145 和 PC3）显示出良好的抗癌活性。除了改变细胞周期的 SubG1、G1/S 和 G2/M 期外，它们的作用主要与抑制细胞活力有关，可能是通过细胞凋亡。在比较 5 号化合物（RCDFC）和 4 号化合物（RC10）对 HUVEC 非肿瘤细胞的细胞毒性作用时，发现 5 号化合物（RCDFC）比 4 号化合物（RC10）更具选择性。未来的工作还应该测试这些化合物与其他化疗药物的结合，以评估它们对进一步敏化耐药转移性 PCa 细胞的作用。
• 一种双散沫花素的制备方法
  申请人：华东师范大学

  公开号：CN107011142A

  公开（公告）日：2017-08-04

  本发明公开了一种双散沫花素的制备方法，其特点是该方法将2‑羟基‑1,4萘醌在有机溶剂中与三聚甲醛混合，在浓硫酸的催化作用下进行双散沫花素的合成反应，所述合成在0~80℃温度下，搅拌反应6~8小时；所述2‑羟基‑1,4萘醌与三聚甲醛、有机溶剂和硫酸的摩尔体积比为：1mmol:0.4mmol~1.2mmol:5~25mL:0.20~5 mL；所述有机溶剂为环己烷、二氯甲烷、冰醋酸或乙醇；所述硫酸的质量浓度为98%。本发明与现有技术相比具有工艺简单，收率高，生产成本低，反应条件更温和，有效避免合成过程中向环境释放有毒的甲醛气体而污染环境，是一种绿色环保、经济高效的双散沫花素合成方法。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• Convergent paired electrosynthesis of different types of bis-β-diketone derivatives based on the knoevenagel condensation reaction under green conditions
  作者：Mahmood Masoudi-Khoram、Mitra Zargarian、Davood Nematollahi、Mohammad Ali Zolfigol、Hassan Sepehrmansourie、Sadegh Khazalpour

  DOI：10.1016/j.electacta.2022.141512

  日期：2023.1

  method, the electrochemical oxidation of primary alcohols to the corresponding aldehydes have taken at anode and the reduction of β-diketones to active methylene compounds has happened in cathode. In next step, the cathodically activated methylene reacts with anodically generated aldehyde. Different types of bis-β-diketones have been synthesized using C1–C5 primary alcohols and different β-diketones

  已经开发了一种绿色收敛配对电化学方案，用于通过 Knoevenagel 缩合反应合成一些双-β-二酮。在该方法中，伯醇在阳极发生电化学氧化为相应的醛，β-二酮在阴极被还原为活性亚甲基化合物。在下一步中，阴极活化的亚甲基与阳极产生的醛反应。已经使用 C1-C5 伯醇和不同的 β-二酮合成了不同类型的双-β-二酮。在这项工作中，我们提出了一种独特的收敛配对机制，用于基于可能的阳极和阴极反应合成双-β-二酮。还优化了溶液pH、电流密度、电极材料、酒精浓度和电池类型等有效参数。