N-(2-aminoethyl)-4-[5-(4-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2-aminoethyl)-4-[5-(4-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
• 英文别名: TT101；N-(2-aminoethyl)-4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
• 化学式: C₁₉H₁₉F₃N₄O₂S
• 分子量: 424.447
• InChiKey: WJAQGYRBBAFZJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(2-aminoethyl)-4-[5-(4-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide 、 丹酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.08h， 生成 5-(dimethylamino)-N-[2-[[4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonylamino]ethyl]naphthalene-1-sulfonamide
  参考文献：
  名称：

  Hybrid fluorescent conjugates of COX-2 inhibitors: Search for a COX-2 isozyme imaging cancer biomarker

  摘要：

  The observation that the cyclooxygenase-2 (COX-2) isozyme is over-expressed in multiple types of cancer, relative to that in adjacent non-cancerous tissue, prompted this investigation to prepare a group of hybrid fluorescent conjugates wherein the COX inhibitors ibuprofen, (S)-naproxen, acetyl salicylic acid, a chlororofecoxib analog and celecoxib were coupled via a linker group to an acridone, dansyl or rhodamine B fluorophore. Within this group of compounds, the ibuprofen-acridone conjugate (10) showed potent and selective COX-2 inhibition (COX-2 IC50 = 0.67 mu M; SI = 110.6), but its fluorescence emission (lambda(em) = 417, 440 nm) was not suitable for fluorescent imaging of cancer cells that over-express the COX-2 isozyme. In comparison, the celecoxib-dansyl conjugate (25) showed a slightly lower COX-2 potency and selectivity (COX-2 IC50 = 1.1 mu M; SI > 90) than the conjugate 10, and it possesses a better fluorescence emission (lambda(em) = 500 nm). Ultimately, a celecoxib-rhodamine B conjugate (28) that exhibited moderate COX-2 potency and selectivity (COX-2 IC50 = 3.9 mu M; SI > 25) having the best fluorescence emission (lambda(em) = 580 nm) emerged as the most promising biomarker for fluorescence imaging using a colon cancer cell line that over-expresses the COX-2 isozyme. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.131
• 作为产物：
  描述：

  4-[5-(4-甲基苯基)-3-三氟甲基-1H-吡唑-1-基]苯磺酰氯 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 N-(2-aminoethyl)-4-[5-(4-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
  参考文献：
  名称：

  基于Celecoxib–NBD的18F标签放射性示踪剂的设计，合成和评估，用于环氧合酶2（COX-2）的正电子发射断层扫描（PET）成像

  摘要：

  根据先前报道的荧光COX-2成像剂celecoxib-NBD（3； NBD = 7-硝基-硝基苯并呋喃），设计和合成了一系列新型的含氟环氧合酶-2（COX-2）抑制剂。体外COX-1 / COX-2抑制的数据显示，ñ - （4-氟苄基）-4-（5- p -甲苯基-3-三氟甲基吡唑-1-基）苯磺酰胺（5 ; IC 50 = 0.36μ中号，SI > 277）和ñ -氟-4-（5- p -甲苯基-3-三氟甲基吡唑-1-基）苯磺酰胺（6 ; IC 50 = 0.24μ中号，SI> 416）是有效的和选择性COX-2抑制剂。化合物5选择使用短寿命的正电子发射器Fluor-18（18 F）进行放射性标记，并作为正电子发射断层扫描（PET）成像剂进行评估。使用人类结直肠癌模型HCA-7在体外和体内对Radiotracer [ 18 F] 5进行了分析。尽管放射性示踪剂对表达COX-2的HCA-7细胞的

  DOI：

  10.1002/cmdc.201500287

文献信息

• Methods for enhancing antigen-specific immune responses
  申请人：The Johns Hopkins University

  公开号：US10799579B2

  公开（公告）日：2020-10-13

  Described herein are methods comprising administering to a mammalian subject an effective amount of an annexin chimeric fusion protein, wherein the annexin chimeric fusion protein comprises at least one immunogenic antigen, thereby enhancing the antigen specific immune response relative to administration of the immunogenic antige alone. Methods and kits for treating or preventing recurrence of hyper proliferating diseases, e.g., cancer, are described. A method may comprise priming a mammal by administering to the mammal an effective amount of a chemotherapeutic agent and boosting the mammal by administering to the mammal an effective amount of an annexin chimeric fusion.

  本文描述的方法包括向哺乳动物施用有效量的附件蛋白嵌合体融合蛋白，其中附件蛋白嵌合体融合蛋白包含至少一种免疫原性抗原，从而相对于单独施用免疫原性抗原增强抗原特异性免疫反应。本文描述了治疗或预防过度增殖疾病（如癌症）复发的方法和试剂盒。一种方法可包括通过向哺乳动物施用有效量的化疗剂来启动哺乳动物，以及通过向哺乳动物施用有效量的附件蛋白嵌合体融合物来增强哺乳动物。
• COMPOSITIONS AND METHODS FOR ENHANCING ANTIGEN-SPECIFIC IMMUNE RESPONSES
  申请人：The Johns Hopkins University

  公开号：EP2424990A2

  公开（公告）日：2012-03-07
• DNA Vaccine Enhancement with MHC Class II Activators
  申请人：Wu Tzyy-Choou

  公开号：US20090093050A1

  公开（公告）日：2009-04-09

  Methods for treating or preventing hyperproliferating diseases, e.g., cancer, are described. A method may comprise administering to a subject in need thereof a therapeutically effective amount of a nucleic acid encoding an MHC class I and/or II activator and optionally a nucleic acid encoding an antigen.
• Anticancer Combination Therapies
  申请人：Wu Tzyy-Choou

  公开号：US20100330105A1

  公开（公告）日：2010-12-30

  Methods for treating or preventing hyperproliferating diseases, e.g., cancer, are described. A method may comprise administering to a subject in need thereof a therapeutically effective amount of a chemotherapeutic agent and a DNA vaccine.
• METHODS FOR ENHANCING ANTIGEN-SPECIFIC IMMUNE RESPONSES
  申请人：Wu Tzyy-Choou

  公开号：US20120225090A1

  公开（公告）日：2012-09-06

  Methods for delivering naked DNA vaccines to enhance immune responses, by improving transfection efficiency without safety concerns associated with live viral vectors, are described. A method may comprise administering to a mammalian subject an effective amount of a papillomavirus pseudovirion, wherein the papillomavirus pseudovirion comprises at least one papillomavirus capsid protein encapsidating a naked DNA vaccine, wherein the naked DNA vaccine comprises a first nucleic acid encoding at least one antigen, thereby enhancing the antigen specific immune response relative to administration of the naked DNA vaccine.