N-(4-aminobutyl)naphthalen-1-amine | 1159836-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-aminobutyl)naphthalen-1-amine
• 英文别名: N1-(naphthalen-1-yl)butane-1,4-diamine；N'-naphthalen-1-ylbutane-1,4-diamine
• CAS: 1159836-46-0
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: JNDGLZQRASTEKF-UHFFFAOYSA-N

物化性质

• 沸点：
  398.3±25.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-aminobutyl)naphthalen-1-amine 在 盐酸 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.67h， 生成 N-[4-(9-dimethylimino-9H-benzo[a]phenoxazin-5-ylamino)butyl]-2-(3,4-bis(4-methoxyphenyl)isoxazol-5-yl)acetamide chloride
  参考文献：
  名称：

  [EN] MOFEZOLAC DERIVATIVES AS MULTI-FUNCTIONS SELECTIVE COX-1 INHIBITORS
  [FR] DÉRIVÉS DE MOFÉZOLAC EN TANT QU'INHIBITEURS SÉLECTIFS À FONCTIONS MULTIPLES DE COX-1

  摘要：

  本发明涉及一类新的化合物，其化学式为（I），用于靶向COX-1。本发明还涉及使用其中一些化合物作为研究该酶的结构和功能的工具，在治疗靶向COX-1或检测与癌症和神经炎症等相关的疾病或疾病中的COX-1，特别是在神经学（例如自闭症谱系障碍）和神经退行性疾病（例如阿尔茨海默病，帕金森病，肌萎缩性侧索硬化症（ALS），多发性硬化症（MS），创伤性脑损伤（TBI），HIV痴呆和朊病）以及妇科肿瘤（例如卵巢癌），颈部和头部肿瘤和血液系统肿瘤（例如多发性骨髓瘤）和检测“体外”（细胞和组织）和“体内”的COX-1。

  公开号：

  WO2017187352A1
• 作为产物：
  描述：

  4-(naphthalen-1-ylamino)butanenitrile 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以72%的产率得到N-(4-aminobutyl)naphthalen-1-amine
  参考文献：
  名称：

  An Efficient Synthesis of N-Arylputrescines and Cadaverines

  摘要：

  我们介绍了一种通过碳酸铯介导的苯胺与Ï-氯腈的烷基化反应以及随后的还原反应，分两步合成 N-芳基putrescines 和adaverines 的通用方法。铯介导的烷基化反应对单烷基化产物具有显著的选择性。该方法简便易行，并能获得令人满意的总产率。

  DOI：

  10.1055/s-0028-1087817

文献信息

• Harnessing GLUT1‐Targeted Pro‐oxidant Ascorbate for Synergistic Phototherapeutics
  作者：Seyoung Koo、Min‐Goo Lee、Amit Sharma、Mingle Li、Xingcai Zhang、Kanyi Pu、Sung‐Gil Chi、Jong Seung Kim

  DOI：10.1002/anie.202110832

  日期：2022.4.19

  phototherapy. AA-EtNBS undergoes a reversible structural conversion of the ascorbate moiety in response to the redox environment, leading to a GLUT1-targeted pro-oxidant effect and synergistic phototherapeutic efficacy.

  5-O-取代的抗坏血酸-光敏剂偶联物AA-EtNBS证明了在 GLUT1 靶向抗癌光疗中利用抗坏血酸化学的好处。AA-EtNBS响应于氧化还原环境经历了抗坏血酸部分的可逆结构转换，导致 GLUT1 靶向促氧化作用和协同光疗功效。
• MOFEZOLAC DERIVATIVES AS MULTI-FUNCTIONS SELECTIVE COX-1 INHIBITORS
  申请人：Università degli Studi di Bari "Aldo Moro"

  公开号：EP3782990A1

  公开（公告）日：2021-02-24

  The invention relates to a new class of compounds targeting COX-1. The invention also relates to the use of some of such compounds as a tool to investigate the structure and function of the enzyme, in the treatment targeting COX-1 or detection of COX-1 in relating disorders or diseases such as cancer and neuroinflammation, in particular in neurological (e.g. autism spectrum disorders) and neurodegenerative diseases (e.g. Alzheimer's diseases, Parkinson's diseases, amyotrophic lateral sclerosis (ALS), multiple sclerosis (MS), traumatic brain injury (TBI), HIV dementia and prion diseases), and in gynecological tumour (e.g. ovarian cancer), neck and head tumor, and haematological tumours (e.g. multiple myeloma) and in the detection of COX-1 in "in vitro" (cells and tissues) and in "in vivo".

  本发明涉及一类靶向 COX-1 的新型化合物。本发明还涉及将其中一些化合物用作研究酶的结构和功能的工具，用于靶向 COX-1 的治疗或检测 COX-1 在癌症和神经炎症等相关紊乱或疾病中的作用，特别是在神经系统疾病（如自闭症谱系障碍）和神经退行性疾病（如阿尔茨海默病、帕金森病、肌萎缩性侧索硬化症（ALS）、多发性硬化症（MLS））中的作用。阿尔茨海默病、帕金森病、肌萎缩性脊髓侧索硬化症（ALS）、多发性硬化症（MS）、创伤性脑损伤（TBI）、艾滋病痴呆症和朊病毒病），以及妇科肿瘤（如卵巢癌）、颈部和头部肿瘤和血液肿瘤（如多发性骨髓瘤），以及在 "体外"（细胞和组织）和 "体内 "检测 COX-1。
• Targeting COX-1 by mofezolac-based fluorescent probes for ovarian cancer detection
  作者：Antonio Scilimati、Savina Ferorelli、Maria Clara Iaselli、Morena Miciaccia、Maria Laura Pati、Cosimo G. Fortuna、Ansari M. Aleem、Lawrence J. Marnett、Maria Grazia Perrone

  DOI：10.1016/j.ejmech.2019.06.039

  日期：2019.10

  Biomarkers of specific targets are becoming an essential objective for clinical unmet clinical needs to improve diseases early detection and increase patient overall survival. Ovarian cancer is among the highest mortality gynecological cancers. It is asymptomatic and almost always diagnosed at advanced stage. At five years from the first diagnosis the survival rate of ovarian cancer patients is only 30%. Cyclooxygenase (COX)-1 as opposed to COX-2 is known to be overexpressed in ovarian cancer. Therefore, fluorescent probes targeting COX-1 were designed and prepared in fair to good yields for its quantitatively detection in human ovarian cancer cell lines (OVCAR-3 and SKOV-3). In particular, both cyto-fluorimetric and immunofluorescent experiments showed that N-[4-(9-dimethylimino-9H-benzo[a] phenoxazin-5-ylamino)butyl]-2-(3,4-bis(4-methoxyphenypisoxazol-5-yl)acetamide chloride (11) enters into OVCAR-3 cells and is mainly localized on the membrane containing the COX-1. Membrane fluorescence emission represents about 80% of the total fluorescence measured in the whole cell, while the nonspecific labeling represents only 20%. This result indicates that the intensity of fluorescence emission is almost exclusively attributable to 11 bound to COX-1 located on the membrane. Furthermore, no diffusion inside the cell occurs. IC50 hCOX-1 value of 11 determined by measuring the O-2 consumption during the bis-oxygenation of the arachidonic acid catalysed by COX-1 was found to be equal to 1.8 nM. Furthermore, 11 inhibits oCOX-1 with IC50 = 6.85 nM and mCOX-2 with IC50 = 269.5 nM; the corresponding selectivity index SI is equal to 39.3 against oCOX-1. 11 inhibits oCOX-1 at 0 min of incubation with 91% inhibition, whereas in the same time it does not inhibit mCOX-2. Fingerprints for Ligands and Proteins (FLAP) software calculations were performed to justify 11 higher COX-1 inhibitory potency than mofezolac (COX-1 IC50 = 5.1 nM), which in turn is a moiety of 11. Specifically, the two compounds bind differently in the COX-1 active site. (C) 2019 Elsevier Masson SAS. All rights reserved.
• [EN] MOFEZOLAC DERIVATIVES AS MULTI-FUNCTIONS SELECTIVE COX-1 INHIBITORS<br/>[FR] DÉRIVÉS DE MOFÉZOLAC EN TANT QU'INHIBITEURS SÉLECTIFS À FONCTIONS MULTIPLES DE COX-1
  申请人：UNIVERSITA' DEGLI STUDI DI BARI ALDO MORO

  公开号：WO2017187352A1

  公开（公告）日：2017-11-02

  The invention relates to a new class of compounds of formula (I) targeting COX-1. The invention also relates to the use of some of such compounds as a tool to investigate the structure and function of the enzyme, in the treatment targeting COX-1 or detection of COX-1 in relating disorders or diseases such as cancer and neuroinflammation, in particular in neurological (e.g. autism spectrum disorders) and neurodegenerative diseases (e.g. Alzheimer's diseases, Parkinson's diseases, amyotrophic lateral sclerosis (ALS), multiple sclerosis (MS), traumatic brain injury (TBI), HIV dementia and prion diseases), and in gynecological tumour (e.g. ovarian cancer), neck and head tumor, and haematological tumours (e.g. multiple myeloma) and in the detection of COX-1 in "in vitro" (cells and tissues) and in "in vivo".

  本发明涉及一类新的化合物，其化学式为（I），用于靶向COX-1。本发明还涉及使用其中一些化合物作为研究该酶的结构和功能的工具，在治疗靶向COX-1或检测与癌症和神经炎症等相关的疾病或疾病中的COX-1，特别是在神经学（例如自闭症谱系障碍）和神经退行性疾病（例如阿尔茨海默病，帕金森病，肌萎缩性侧索硬化症（ALS），多发性硬化症（MS），创伤性脑损伤（TBI），HIV痴呆和朊病）以及妇科肿瘤（例如卵巢癌），颈部和头部肿瘤和血液系统肿瘤（例如多发性骨髓瘤）和检测“体外”（细胞和组织）和“体内”的COX-1。
• An Efficient Synthesis of <i>N</i>-Arylputrescines and Cadaverines
  作者：Liliana Orelli、Natalia Link、Jimena Díaz

  DOI：10.1055/s-0028-1087817

  日期：——

  We present a two-step, general synthesis of N-aryl­putrescines and cadaverines, by cesium carbonate mediated alkylation of anilines with ω-chloronitriles and subsequent reduction. The cesium-mediated alkylation shows remarkable selectivity towards the monoalkylation product. The method is straightforward and leads to satisfactory global yields.

  我们介绍了一种通过碳酸铯介导的苯胺与Ï-氯腈的烷基化反应以及随后的还原反应，分两步合成 N-芳基putrescines 和adaverines 的通用方法。铯介导的烷基化反应对单烷基化产物具有显著的选择性。该方法简便易行，并能获得令人满意的总产率。