2-氨基-5-(3-呋喃基)-1,3,4-恶二唑 | 1016511-08-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-氨基-5-(3-呋喃基)-1,3,4-恶二唑
• 英文名称: 5-(furan-3-yl)-1,3,4-oxadiazol-2-amine
• 英文别名: 2-amino-5-(3-furyl)-1,3,4-oxadiazole
• CAS: 1016511-08-2
• 化学式: C₆H₅N₃O₂
• 分子量: 151.125
• InChiKey: QARBJYAEPHCALY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 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：
  78.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-苯基-4-喹啉羧酸 、 2-氨基-5-(3-呋喃基)-1,3,4-恶二唑 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[5-(3-furyl)-1,3,4-oxadiazol-2-yl]-2-phenyl-4-quinoline carboxamide
  参考文献：
  名称：

  Identification of a New Series of STAT3 Inhibitors by Virtual Screening

  摘要：

  The signal transducer and activator of transcription 3 (STAT3) is considered to be an attractive therapeutic target for oncology drug development. We identified a N-[2-(1,3,4-oxadiazolyl)]-4-quinolinecarboxamide derivative, STX-0119, as a novel STAT3 dimerization inhibitor by a virtual screen using a customized version of the DOCK4 program with the crystal structure of STAT3 In addition, we used in vitro cell-based assays such as the luciferase reporter gene assay and the fluorescence resonance energy transfer-based STAT3 dimerization assay STX-0119 selectively abrogated the DNA binding activity of STAT3 and suppressed the expression of STAT3-regulated oncoproteins such as c-myc and survivin in cancer cells. In contrast a truncated inactive analogue, STX-0872, did not exhibit those activites, Oral administration of STX-0119 effectively abrogated the growth of human lymphoma cells in a SCC-3 subcutaneous xenograft model without visible toxicity Structure-activity relationships of STX-0119 derivatives were investigated using the docking model of the STAT3-SH2 domain/STX-0119.

  DOI：

  10.1021/ml1000273
• 作为产物：
  描述：

  3-糠酸 在 氯化亚砜 、 1,3-二溴-5,5-二甲基海因 、 potassium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 、 甲苯 为溶剂， 反应 4.0h， 生成 2-氨基-5-(3-呋喃基)-1,3,4-恶二唑
  参考文献：
  名称：

  STAT3 INHIBITOR CONTAINING QUINOLINECARBOXAMIDE DERIVATIVE AS ACTIVE INGREDIENT

  摘要：

  公开号：

  EP2325181B1

文献信息

• PRODUCTION METHOD OF QUINOLINECARBOXAMIDE DERIVATIVE OR PRODUCTION INTERMEDIATE THEREOF
  申请人：KABUSHIKI KAISHA YAKULT HONSHA

  公开号：US20220169640A1

  公开（公告）日：2022-06-02

  Provided is a method for industrially advantageously synthesizing a production intermediate of a quinolinecarboxamide derivative or a salt thereof. The present invention provides a method for producing a quinolinecarboxylic acid derivative of formula (4) or a salt thereof, including reacting an aniline of the following formula (1), in the presence of boron trifluoride-tetrahydrofuran complex or boron trifluoride-diethyl ether complex, with an aldehyde of formula (2) and subsequently reacting the resulting compound with an α-keto acid of formula (3), wherein R 1 , R 2 , R 3 and R 4 are the same or different and each represent a hydrogen atom, a halogen atom, a lower alkyl group, or the like, R 5 represents a hydrogen atom, a lower alkyl group, or the like, and R 6 represents a hydrogen atom, a lower alkyl group, or the like.

  提供了一种工业上优势合成喹啉羧酰胺衍生物或其盐的生产中间体的方法。本发明提供了一种制备喹啉羧酸衍生物的方法，其化学式为（4）或其盐，包括在三氟化硼-四氢呋喃复合物或三氟化硼-二乙醚复合物的存在下，用化学式（1）的苯胺与化学式（2）的醛反应，然后用化学式（3）的α-酮酸反应所得化合物，其中R1、R2、R3和R4相同或不同，每个代表氢原子、卤素原子、低级烷基或类似物，R5代表氢原子、低级烷基或类似物，R6代表氢原子、低级烷基或类似物。
• STAT3 inhibitor containing quinolinecarboxamide derivative as active ingredient
  申请人：Asai Akira

  公开号：US08466290B2

  公开（公告）日：2013-06-18

  The present invention provides a STATS inhibitor containing as an active ingredient, a quinolinecarboxamide derivative represented by the formula (I) (in the formula, W represents a bond or an alkylene chain; X represents O, S, or NR34; and R1 to R8 and R34 each represent H, halogen, alkyl, phenyl, furyl, thienyl, or the like), or a pharmacologically acceptable salt thereof.

  本发明提供了一种STATS抑制剂，其含有一种以公式(I)表示的喹啉羧酰胺衍生物作为活性成分（在公式中，W表示键或烷基链；X表示O，S或NR34；R1至R8和R34各自表示H，卤素，烷基，苯基，呋喃基，噻吩基或类似物），或其药理学上可接受的盐。
• US8466290B2
  申请人：——

  公开号：US8466290B2

  公开（公告）日：2013-06-18
• [EN] PRODUCTION METHOD OF QUINOLINECARBOXAMIDE DERIVATIVE OR PRODUCTION INTERMEDIATE THEREOF<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN DÉRIVÉ QUINOLINECARBOXAMIDE OU D'UN INTERMÉDIAIRE DE PRODUCTION DE CELUI-CI<br/>[JA] キノリンカルボキサミド誘導体又はその製造中間体の製造法
  申请人：YAKULT HONSHA KK

  公开号：WO2020196327A1

  公开（公告）日：2020-10-01

  キノリンカルボキサミド誘導体又はその塩の製造中間体を工業的に有利に合成する方法を提供する。　下記の式（１）で表されるアニリン類に、ボロントリフルオリド－テトラヒドロフラン錯体又はボロントリフルオリド－ジエチルエーテル錯体の存在下、式（２）で表されるアルデヒド類を反応させ、続いて式（３）で表されるα－ケト酸類を反応させることを特徴とする、式（４）で表されるキノリンカルボン酸誘導体又はその塩の製造法。 〔式中、Ｒ１，Ｒ２，Ｒ３及びＲ４は同一又は異なっていてもよく、水素原子、ハロゲン原子、低級アルキル基他、Ｒ５は水素原子、低級アルキル基他、Ｒ６は水素原子、低級アルキル基他。〕
• Identification of a New Series of STAT3 Inhibitors by Virtual Screening
  作者：Kenji Matsuno、Yoshiaki Masuda、Yutaka Uehara、Hiroshi Sato、Ayumu Muroya、Osamu Takahashi、Takane Yokotagawa、Toshio Furuya、Tadashi Okawara、Masami Otsuka、Naohisa Ogo、Tadashi Ashizawa、Chie Oshita、Sachiko Tai、Hidee Ishii、Yasuto Akiyama、Akira Asai

  DOI：10.1021/ml1000273

  日期：2010.11.11

  The signal transducer and activator of transcription 3 (STAT3) is considered to be an attractive therapeutic target for oncology drug development. We identified a N-[2-(1,3,4-oxadiazolyl)]-4-quinolinecarboxamide derivative, STX-0119, as a novel STAT3 dimerization inhibitor by a virtual screen using a customized version of the DOCK4 program with the crystal structure of STAT3 In addition, we used in vitro cell-based assays such as the luciferase reporter gene assay and the fluorescence resonance energy transfer-based STAT3 dimerization assay STX-0119 selectively abrogated the DNA binding activity of STAT3 and suppressed the expression of STAT3-regulated oncoproteins such as c-myc and survivin in cancer cells. In contrast a truncated inactive analogue, STX-0872, did not exhibit those activites, Oral administration of STX-0119 effectively abrogated the growth of human lymphoma cells in a SCC-3 subcutaneous xenograft model without visible toxicity Structure-activity relationships of STX-0119 derivatives were investigated using the docking model of the STAT3-SH2 domain/STX-0119.