1-azido-5-naphthol | 51642-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-azido-5-naphthol
• 英文别名: 5-azido-1-naphtol；5-azidonaphthalen-1-ol
• CAS: 51642-27-4
• 化学式: C₁₀H₇N₃O
• 分子量: 185.185
• InChiKey: ZNXQQRPQXMLNNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-azido-5-naphthol 在 盐酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 2-p-Tolylamino-2H-benzo[cd]indazol-5-one
  参考文献：
  名称：

  Intramolecular cyclization of peri-substituted 1-azidonaphthalenes. 3. Structural and chemical investigation of 1-(arylamino)benz[cd]indazol-8(and 6)(1H)-ones produced by decomposition of hydroxy-substituted 8-azido-1-(arylazo)naphthalenes

  摘要：

  DOI：

  10.1021/jo00132a004
• 作为产物：
  描述：

  (5-hydroxynaphthalen-1-yl)boronic acid 在 sodium azide 、 copper(II) sulfate 作用下， 以 甲醇 为溶剂， 生成 1-azido-5-naphthol
  参考文献：
  名称：

  A novel triazole derivative of betulinic acid induces extrinsic and intrinsic apoptosis in human leukemia HL-60 cells

  摘要：

  In an attempt to arrive at more potent cytotoxic agent than the bioactive natural product betulinic acid, influence of small structural modifications of its 1, 2, 3 triazole derivatives tethered at C-28 and both C3, C-28 using click chemistry approach has been studied. The chemically characterized triazoles have been screened for in vitro cytotoxicity against four human cancer cell lines HL-60, MiaPaCa-2, PC-3 and A549 which has allowed to identify triazole derivative 28{1N (4-fluoro phenyl)-1H-1, 2, 3-triazol-4-yl} methyloxy betulinic ester having better potency profile than the parent compound with IC50 values in the range of 5-7 mu M. It caused disruption of mitochondrial membrane potential, rendered Bcl-2 cleavage, Bax translocation and decrease Bcl-2/Bax ratio. These events are accompanied by activation of caspases -9, similar to 3, which cleave the PARP-1. It also induces caspase-8, which is involved in extrinsic apoptotic pathway. Therefore, it induces apoptosis through both intrinsic and extrinsic pathways in human leukemia HL-60 cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.018

文献信息

• Reduction of organic azides to amines using reusable Fe3O4 nanoparticles in aqueous medium
  作者：Sreenivasarao Pagoti、Subham Surana、Ajay Chauhan、Bibudha Parasar、Jyotirmayee Dash

  DOI：10.1039/c2cy20776a

  日期：——

  Aromatic, heteroaromatic and sulfonyl azides were conveniently reduced to the corresponding amines in excellent yields using hydrazine hydrate in the presence of iron oxide nanoparticles. The Fe3O4-MNPs could be easily separated by an external magnet, and recycled ten times without significant loss of the catalytic efficiency.

  芳香性叠氮化合物、杂芳香性叠氮化合物和磺酰叠氮化合物可以方便地使用在铁氧化物纳米粒子存在下的水合肼还原为相应的胺，产率极佳。Fe3O4-MNPs可以轻松地通过外部磁铁分离，并可循环使用十次而催化效率无显著损失。
• Synthesis of 3-O-propargylated betulinic acid and its 1,2,3-triazoles as potential apoptotic agents
  作者：Rabiya Majeed、Payare L. Sangwan、Praveen K. Chinthakindi、Imran Khan、Nisar A. Dangroo、Niranjan Thota、Abid Hamid、Parduman R. Sharma、Ajit K. Saxena、Surrinder Koul

  DOI：10.1016/j.ejmech.2013.03.028

  日期：2013.5

  carried out on betulinic acid, through concise 1,2,3-triazole synthesis via click chemistry approach at C-3position in ring A have been evaluated for their cytotoxic potentiation against nine human cancer cell lines. Most of the derivatives have shown higher cytotoxic profiles than the parent molecule. Two compounds i.e. 31N(2-cyanophenyl)-1H-1,2,3-triazol-4yl}methyloxy betulinic acid (7) and 31N(5-hyd

  目前，来自自然界的细胞毒性剂是抗癌化学疗法的主要手段，因此迫切需要增强抗癌剂库的需求。已通过在A环C-3位的C-3位置通过单击化学方法通过简明的1,2,3-三唑合成对桦木酸进行的化学转化研究，评估了它们对9种人类癌细胞系的细胞毒性增强作用。大多数衍生物显示出比母体分子更高的细胞毒性谱。两种化合物，即3 1 Ñ（2-氰基苯基）-1 ħ 1,2,3-三唑-4-基}甲氧基桦木酸（7）和3 1 Ñ（5-羟基-萘-1-基）-1 ħ - 1,2,3-三唑-4基}甲氧基苯丁酸（13）对白血病细胞系HL-60表现出令人印象深刻的IC 50值（分别为2.5和3.5μM）（效力比白果酸高5至7倍）。从各种生物学终点来看，证明了对细胞迁移和集落形成的抑制，线粒体膜的破坏，随后的DNA片段化和凋亡。
• Synthesis and chemiluminescent activity of 8,9-dihydrobenzo[g] pyridazino[4,5-b]indole-7,10(11H)-diones
  作者：Masateru Kurumi、Kenji Sasaki、Hiroko Takata、Taiji Nakayama

  DOI：10.1002/jhet.5570380313

  日期：2001.5

  corresponding triazole derivatives, which were converted to dimethyl 1H-benz[g]indole-2,3-dicarboxylates by photocyclization. The reaction of the diesters with hydrazine hydrate gave the corresponding 8,9-dihydrobenzo[g]-pyridazino[4,5-b]indole-7,10(11H)-diones (5). One of compounds 5 was found to have chemiluminescent activity similar to luminol.

  取代的和未取代的萘胺被转化为相应的三唑衍生物，并通过光环化将其转化为1 H-苯并[ g ]吲哚-2,3-二羧酸二甲酯。二酯与水合肼的反应得到相应的8，9-二氢苯并[ g ]-哒嗪并[4，5 - b ]吲哚-7，10 （11H）-二酮（5）。发现化合物5之一具有与鲁米诺相似的化学发光活性。
• MONTEVECCHI, P. C.;SPAGNOLO, P., J. ORG. CHEM., 1982, 47, N 11, 1996-2000
  作者：MONTEVECCHI, P. C.、SPAGNOLO, P.

  DOI：——

  日期：——
• A novel triazole derivative of betulinic acid induces extrinsic and intrinsic apoptosis in human leukemia HL-60 cells
  作者：Imran Khan、Santosh K. Guru、Santosh K. Rath、Praveen K. Chinthakindi、Buddh Singh、Surrinder Koul、Shashi Bhushan、Payare L. Sangwan

  DOI：10.1016/j.ejmech.2015.11.018

  日期：2016.1

  In an attempt to arrive at more potent cytotoxic agent than the bioactive natural product betulinic acid, influence of small structural modifications of its 1, 2, 3 triazole derivatives tethered at C-28 and both C3, C-28 using click chemistry approach has been studied. The chemically characterized triazoles have been screened for in vitro cytotoxicity against four human cancer cell lines HL-60, MiaPaCa-2, PC-3 and A549 which has allowed to identify triazole derivative 281N (4-fluoro phenyl)-1H-1, 2, 3-triazol-4-yl} methyloxy betulinic ester having better potency profile than the parent compound with IC50 values in the range of 5-7 mu M. It caused disruption of mitochondrial membrane potential, rendered Bcl-2 cleavage, Bax translocation and decrease Bcl-2/Bax ratio. These events are accompanied by activation of caspases -9, similar to 3, which cleave the PARP-1. It also induces caspase-8, which is involved in extrinsic apoptotic pathway. Therefore, it induces apoptosis through both intrinsic and extrinsic pathways in human leukemia HL-60 cells. (C) 2015 Elsevier Masson SAS. All rights reserved.