2-amino-3-(phenylthio)-1,4-naphthoquinone | 56908-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-3-(phenylthio)-1,4-naphthoquinone
• 英文别名: 2-amino-3-phenylsulfanyl-[1,4]naphthoquinone；2-amino-3-thiophenyl-1,4-naphthoquinone；2-Amino-3-thiophenyl-1,4-naphthochinon；2-Amino-3-phenylmercapto-[1,4]naphthochinon；2-Amino-3-phenylsulfanyl-naphthalene-1,4-dione；2-amino-3-phenylsulfanylnaphthalene-1,4-dione
• CAS: 56908-66-8
• 化学式: C₁₆H₁₁NO₂S
• 分子量: 281.335
• InChiKey: ZZIAKWNWNFDUEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-phenylsulfanyl-[1,4]naphthoquinone 在 苄氧基胺盐酸盐 、 三乙胺 作用下， 以 乙醇 为溶剂， 以68%的产率得到2-amino-3-(phenylthio)-1,4-naphthoquinone
  参考文献：
  名称：

  Reaction of Hydroxylamines with 1,4-Quinones: A New Direct Synthesis of Aminoquinones

  摘要：

  描述了一种对1,4-萘醌和1,4-苯醌的新型一步胺化反应。O-苄基羟肟酸被认为是最佳的胺化试剂，而O-甲基羟肟酸、羧基甲氧基胺和游离羟肟酸的效果较差。

  DOI：

  10.1055/s-1994-25603

文献信息

• Synthesis and evaluation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones that potently induce apoptosis in cancer cells
  作者：Vishnu K. Tandon、Hardesh K. Maurya、Sandeep Kumar、Aijaz Rashid、Dulal Panda

  DOI：10.1039/c3ra47720g

  日期：——

  4-naphthoquinones by an environmentally benign short synthetic route with the goal of finding 1,4-naphthoquinone derivatives that induce apoptosis in cancer cells. We have identified three most active naphthoquinones 10, 12 and 15 that potently induce apoptosis in human cervical carcinoma (HeLa) cells. One of these three compounds perturbed both microtubule and actin filaments.

  本文描述了通过环境友好的短合成途径制备2-杂芳基和2,3-二杂芳基-1,4-萘醌的方法，目的是寻找诱导癌细胞凋亡的1,4-萘醌衍生物。我们已经确定了三种最活跃的萘醌10、12和15，它们可以有效诱导人宫颈癌（HeLa）细胞凋亡。这三种化合物之一干扰了微管和肌动蛋白丝。
• Reaction of Hydroxylamines with 1,4-Quinones: A New Direct Synthesis of Aminoquinones
  作者：Shmuel Bittner、Dorit Lempert

  DOI：10.1055/s-1994-25603

  日期：——

  A novel one-step amination of 1,4-naphthoquinones and 1,4-benzoquinones is described. O-Benzylhydroxylamine was found to be the best aminating agent while O-methylhydroxylamine, carboxymethoxylamine and free hydroxylamine are less effective.

  描述了一种对1,4-萘醌和1,4-苯醌的新型一步胺化反应。O-苄基羟肟酸被认为是最佳的胺化试剂，而O-甲基羟肟酸、羧基甲氧基胺和游离羟肟酸的效果较差。
• C(sp²)–H bond sulfenylation of aminouracils and enaminones from aryl halides
  作者：N. Nowrouzi、M. Abbasi、E. Shaikhi Shahidzadeh、F. Amaleh

  DOI：10.1039/d1nj05726j

  日期：——

  The first direct access to thioarylated aminouracils and enaminones from aryl halides in the presence of CuI and potassium cyanodithioformate as an effective source of sulfur, via a process which is free from the foul smell of thiol, is described.

  描述了在作为有效硫源的 CuI 和氰基二硫代甲酸钾存在下，通过没有硫醇恶臭的方法，从芳基卤化物中直接获得硫代芳基化氨基尿嘧啶和烯胺酮。
• Efficient aerobic and DMSO-oxidative sulfenylation reactions catalyzed by Na2S2O3
  作者：Habiballah Shafie、Mohammad Abbasi

  DOI：10.1016/j.tet.2024.133989

  日期：2024.5

  Two efficient acid-base-free procedures are introduced for the sulfenylation of cyclic enaminone compounds under aerobic and DMSO-oxidative conditions catalyzed by NaSO. According to procedures, a mixture of an aryl thiol and a cyclic enaminone are reacting together in DMF (aerobic oxidative conditions) or DMSO in the presence of a catalytic amount of NaSO (0.1 equiv in DMSO and 0.4 equiv in DMF) to

  引入了两种有效的无酸碱程序，用于 NaSO 催化的有氧和 DMSO 氧化条件下环状烯胺酮化合物的磺酰化。根据程序，芳基硫醇和环状烯胺酮的混合物在DMF（有氧氧化条件）或DMSO中，在催化量的Na2SO4（DMSO中0.1当量，DMF中0.4当量）存在下一起反应，产生相关的高产率的α-磺酰化环状烯胺酮化合物。在没有 NaSO 的情况下，这两种反应都不能令人满意，因此 DMF（有氧条件）中的反应根本不会产生任何产物，并且 DMSO 中的转化率在 24 小时内进展不到 50%。
• Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents
  作者：Vishnu K. Tandon、Hardesh K. Maurya、Nripendra N. Mishra、Praveen K. Shukla

  DOI：10.1016/j.ejmech.2009.03.006

  日期：2009.8

  A series of 2-Arylamino-3-chloro-1,4-naphthoquinones (3), 2-Amino-3-aryisulfanyl-1,4-naphthoquinones (5), 2-Arylamino-3-arylsulfanyl-1,4-naphthoquinones (6), Dihydrobenzo[f]naphtho[2,3-b][1,4]thiazelpine-6,11-diones (9) (via Pictet-Spengler cyclization), Isoindoline-1,3-dione derivatives of 1,4- naphthoquinone (13), 2,2'-(1,4-Dioxo-1,4-dihydronaphthalene-2,3-diyl)bis(methylene)dibenzonitrile (14), 13-Amino-12-substituted-6H-benzo[e]naphtho [2,3-b][1,4]diazepine-6,11(12H)-diones (15-16), 2-Chloro-3-atylsulfanyl-1,4-naphthoquinones (17-18) and 3-Methyl-6H-benzo[b]phenothiazine-6,11(12H)-dione (19) were synthesized and studied for their antifungal and antibacterial activities. The results indicate that compounds 3b, 5a and 5b have potent antifungal activity. Amongst the most promising antifungal compounds, 3b showed better antifungal activity than clinically prevalent antifungal drug Fluconazole (MIC50 = 2.0 mu g/mL) against Sporothrix schenckii (MIC50 = 1.56 mu g/mL), significant profile against Candida albicans (MIC50 = 1.56 mu g/mL), Cryptococcus neoformans (MIC50 = 0.78 mu g/mL) and Trichophyton mentagraphytes (MIC50 = 1.56 mu g/mL) and same antifungal activity when compared with Amphotericin-B against C. neoformans (MIC50 = 0.78 mu g/mL). Compounds 3b, 5a and 5b also showed promising antibacterial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.