2-((4-硝基苯基)磺酰基)-1,2,3,4-四氢异喹啉 | 64880-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 2-((4-硝基苯基)磺酰基)-1,2,3,4-四氢异喹啉
• 英文名称: 2-((4-nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(4-nitrobenzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline；2-[(4-Nitrophenyl)sulfonyl]-1,2,3,4-tetrahydroisoquinoline；2-(4-nitrophenyl)sulfonyl-3,4-dihydro-1H-isoquinoline
• CAS: 64880-92-8
• 化学式: C₁₅H₁₄N₂O₄S
• mdl: MFCD00784312
• 分子量: 318.353
• InChiKey: GFAJPJGKVNRLNV-UHFFFAOYSA-N

物化性质

• 熔点：
  161 °C(Solv: benzene (71-43-2))
• 沸点：
  515.8±60.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((4-硝基苯基)磺酰基)-1,2,3,4-四氢异喹啉 在 potassium carbonate 、 巯基乙酸 作用下， 以 甲醇 为溶剂， 以98%的产率得到四氢异喹啉
  参考文献：
  名称：

  Practical and Cost-Effective Manufacturing Route for the Synthesis of a β-Lactamase Inhibitor

  摘要：

  Compound 1, a potent and irreversible inhibitor of beta-lactamases, is in clinical trials with beta-lactam antibiotics for the treatment of serious and antibiotic-resistant bacterial infections. A short, scalable, and cost-effective route for the production of this densely functionalized polycyclic molecule is described.

  DOI：

  10.1021/ol4031606
• 作为产物：
  描述：

  对硝基苯磺酰氯 在 甲酸 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-((4-硝基苯基)磺酰基)-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  Novel 1,4-naphthoquinone-based sulfonamides: Synthesis, QSAR, anticancer and antimalarial studies

  摘要：

  A novel series of 1,4-naphthoquinones (33-44) tethered by open and closed chain sulfonamide moieties were designed, synthesized and evaluated for their cytotoxic and antimalarial activities. All quinone-sulfonamide derivatives displayed a broad spectrum of cytotoxic activities against all of the tested cancer cell lines including HuCCA-1, HepG2, A549 and MOLT-3. Most quinones (33-36 and 38-43) exerted higher anticancer activity against HepG2 cell than that of the etoposide. The open chain analogs 36 and 42 were shown to be the most potent compounds. Notably, the restricted sulfonamide analog 38 with 6,7-dimethoxy groups exhibited the most potent antimalarial activity (IC50 = 2.8 mu M). Quantitative structure activity relationships (QSAR) study was performed to reveal important chemical features governing the biological activities. Five constructed QSAR models provided acceptable predictive performance (R-cv, 0.5647-0.9317 and RMSEcv 0.1231-0.2825). Four additional sets of structurally modified compounds were generated in silico (34a-34d, 36a-36k, 40a-40d and 42a-42k) in which their activities were predicted using the constructed QSAR models. A comprehensive discussion of the structure activity relationships was made and a set of promising compounds (i.e., 33, 36, 38, 42, 36d, 36f, 42e, 42g and 42f) was suggested for further development as anticancer and antimalarial agents. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.001

文献信息

• [EN] SMALL MOLECULE ACTIVATORS OF NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE (NAMPT) AND USES THEREOF<br/>[FR] ACTIVATEURS À PETITES MOLÉCULES DE NICOTINAMIDE PHOSPHORIBOSYLTRANSFÉRASE (NAMPT) ET LEURS UTILISATIONS
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2018132372A1

  公开（公告）日：2018-07-19

  Provided herein are small molecule activators of Nicotinamide Phosphoribosyltransferase (NAMPT), compositions comprising the compounds, and methods of using the compounds and compositions.

  本文提供了尼古丁酰胺磷酸核糖转移酶（NAMPT）的小分子激活剂，包括这些化合物的组合物，以及使用这些化合物和组合物的方法。
• 10.1039/d4ob00807c
  作者：Wen, Xiang、Ma, Yidong、Chen, Jie、Wang, Bin

  DOI：10.1039/d4ob00807c

  日期：——

  We report herein a synthetically useful catalytic system for aliphatic C–H oxidation with a mononuclear nonheme cobalt(II) complex and m-chloroperbenzoic acid (m-CPBA). Preliminary mechanistic studies suggest that a high-valent cobalt–oxygen species (e.g., cobalt(IV)-oxo or cobalt(III)-oxyl) is the oxidant that effects C–H oxidation via a rate-determining hydrogen atom abstraction (HAA) step.

  我们在此报告了一种用于脂肪族 C-H 氧化的合成有用的催化系统，该系统使用单核非血红素钴 ( II ) 络合物和间氯过苯甲酸 ( m -CPBA)。初步机理研究表明，高价钴-氧物种（例如，钴（ IV ）-氧代或钴（ III ）-氧基）是通过决定速率的氢原子夺取（HAA）影响C-H氧化的氧化剂步。
• A Facile Synthesis of 5,6-Dihydro-4H-pyrrolo[3,4-d]thiazole and Other Pyrrolidine-Fused Aromatic Ring Systems via One-Step Cyclization from Diols
  作者：Kenji Yoshikawa、Tsutomu Nagata、Toshiharu Yoshino、Noriyasu Haginoya、Ryo Muto、Akiyoshi Mochizuki、Toshiharu Ohta

  DOI：10.3987/com-12-12481

  日期：——

  A facile synthetic method of 5,6-dihydro-4H-pyrrolo[3,4-d]thiazole, which is a subunit of a potent factor Xa (fXa) inhibitor was developed. This new approach employs one-step cyclization from a diol and can be applied to the syntheses of other pyrrolidine-fused aromatic ring sytems.
• Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity
  作者：Ratchanok Pingaew、Prasit Mandi、Chanin Nantasenamat、Supaluk Prachayasittikul、Somsak Ruchirawat、Virapong Prachayasittikul

  DOI：10.1016/j.ejmech.2014.05.019

  日期：2014.6

  A novel series of N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinolines (14-33) containing triazole moiety were designed and synthesized through rational cycloadditions using the modified Pictet-Spengler reaction and the Click chemistry. Antiproliferative activity against four cancer cell lines (e.g., HuCCA-1, HepG2, A549 and MOLT-3) revealed that many substituted triazole analogs of benzoates (20, 29) and benzaldehydes (30,32) exhibited anticancer activity against all of the tested cancer cell lines in which the ester analog 20 was shown to be the most potent compound against HuCCA-1 (IC50=0.63 mu M) and A549 (IC50 = 0.57 mu M) cell lines. Triazoles bearing phenyl (15, 24), tolyl (26, 27), acetophenone (19), benzoate (20, 29), benzaldehyde (21, 30) and naphthalenyl (25) substituents showed stronger anticancer activity against HepG2 cells than that of the etoposide. Interestingly, the p-tolyl analog (27) displayed the most potent inhibitory activity (1050 = 0.56 mu M) against HepG2 cells without affecting normal cells. Of the investigated tetrahydroisoquinoline-triazoles, the promising compounds 20 and 27 were selected for molecular docking against AKR1C3, which was identified to be a plausible target site. (C) 2014 Elsevier Masson SAS. All rights reserved.
• In Vitro and in Vivo Antileishmanial and Trypanocidal Studies of New <i>N</i>-Benzene- and <i>N</i>-Naphthalenesulfonamide Derivatives
  作者：Cristina Galiana-Roselló、Pablo Bilbao-Ramos、M. Auxiliadora Dea-Ayuela、Miriam Rolón、Celeste Vega、Francisco Bolás-Fernández、Enrique García-España、Jorge Alfonso、Cathia Coronel、M. Eugenia González-Rosende

  DOI：10.1021/jm4006127

  日期：2013.11.27

  We report in vivo and in vitro antileishmanial and trypanocidal activities of a new series of N-substituted benzene and naphthalenesulfonamides 1-15. Compounds 1-15 were screened in vitro against Leishmania infantum, Leishmania braziliensis, Leishmania guyanensis, Leishmania amazonensis, and Trypanosoma cruzi. Sulfonamides 6e, 10b, and 10d displayed remarkable activity and selectivity toward T. cruzi epimastigotes and amastigotes. 6e showed significant trypanocidal activity on parasitemia in a murine model of acute Chagas disease. Moreover, 6e, 8c, 9c, 12c, and 14d displayed interesting IC50 values against Leishmania spp promastigotes as well as L. amazonensis and L. infantum amastigotes. 9c showed excellent in vivo activity (up to 97% inhibition of the parasite growth) in a short-term treatment murine model for acute infection by L. infantum. In addition, the effect of compounds 9c and 14d on tubulin as potential target was assessed by confocal microscopy analysis applied to L. infantum promastigotes.