2-(1-acetyl-3-((4-((2-ethylquinolin-4-yl)methoxy)phenyl)sulfonamido)azetidin-3-yl)-N-hydroxyacetamide | 24260-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(1-acetyl-3-((4-((2-ethylquinolin-4-yl)methoxy)phenyl)sulfonamido)azetidin-3-yl)-N-hydroxyacetamide
• 英文别名: 2-ethylquinoline-4-carboxylic acid；2-ethyl-quinoline-4-carboxylic acid；2-Aethyl-chinolin-4-carbonsaeure；2-Ethyl-cinchoninsaeure
• CAS: 24260-30-8
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD00455441
• 分子量: 201.225
• InChiKey: NURFUWUIIYWPKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-acetyl-3-((4-((2-ethylquinolin-4-yl)methoxy)phenyl)sulfonamido)azetidin-3-yl)-N-hydroxyacetamide 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-chloromethyl-2-ethylquinoline
  参考文献：
  名称：

  用于牛皮癣局部治疗的新型TACE抑制剂的发现和工艺开发

  摘要：

  靶向TNFα途径是治疗牛皮癣的有效方法。在这一途径中，TACE成为可药物治疗的目标，并且一直是内部研究计划的重点。在本文中，我们介绍了临床候选药物26a的发现。从溶解度或基因毒性差的命中开始，通过彻底的多参数优化确定了26a。在恶唑酮介导的炎症模型中显示出强大的体内活性，因此选择了该化合物进行开发。经过多晶型物筛选后，选择盐酸盐，并有效地进行了合成，以API的总收率达到47％。

  DOI：

  10.1016/j.bmc.2017.07.054
• 作为产物：
  描述：

  2-(1-甲氧基-乙基)-喹啉-4-羧酸 在 磷化氢 、 氢碘酸 作用下， 生成 2-(1-acetyl-3-((4-((2-ethylquinolin-4-yl)methoxy)phenyl)sulfonamido)azetidin-3-yl)-N-hydroxyacetamide
  参考文献：
  名称：

  Utilization of Alkoxy Ketones in the Synthesis of Quinolines by the Pfitzinger Reaction. II¹

  摘要：

  DOI：

  10.1021/ja01260a041

文献信息

• Studies on novel 2-imidazolidinones and tetrahydropyrimidin-2(1H)-ones as potential TACE inhibitors: Design, synthesis, molecular modeling, and preliminary biological evaluation
  作者：Shirshendu DasGupta、Prashant R. Murumkar、Rajani Giridhar、Mange Ram Yadav

  DOI：10.1016/j.bmc.2009.04.003

  日期：2009.5

  tetrahydropyrimidin-2(1H)-ones were synthesized and evaluated for their TACE inhibitory activity. Most of the compounds showed very good TACE inhibitory activity. Docking study clearly indicates importance of the P1′ group of the inhibitor for the TACE inhibitory activity. This work proves that these two classes of molecules could be used as potential leads for the development of TACE inhibitors.

  合成属于2-咪唑啉酮和四氢嘧啶-2（1 H）-一类的化合物，并评价其TACE抑制活性。大多数化合物显示出非常好的TACE抑制活性。对接研究清楚地表明了抑制剂的P1'基团对TACE抑制活性的重要性。这项工作证明这两类分子可用作开发TACE抑制剂的潜在先导。
• Arylmethylene Substituted N-Acyl-Beta-Amino Alcohols
  申请人：WORTMANN Lars

  公开号：US20090082372A1

  公开（公告）日：2009-03-26

  The present invention relates to arylmethylene substituted N-Acyl-β-amino alcohols of the formula I in which Y is selected from the aryl or heteroaryl groups: and R1, R2, R3, R4, R5, Q, X and W have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

  本发明涉及公式I的芳基亚甲基取代的N-酰基-β-氨基醇化合物，其中Y选自芳基或杂芳基基团：R1，R2，R3，R4，R5，Q，X和W的含义如描述中所定义。本发明的化合物是有效的FSH拮抗剂，例如可用于男性或女性的生育控制，或用于骨质疏松症的预防和/或治疗。
• 2,3,4,9-TETRAHYDRO-1H-CARBAZOLES
  申请人：Wortmann Lars

  公开号：US20080275083A1

  公开（公告）日：2008-11-06

  The present invention relates to 2,3,4,9-tetrahydro-1H-carbazoles of the general formula I, in which Q, X, W, R1, R2, R3, R4 and R5 have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

  本发明涉及通式I中的2,3,4,9-四氢-1H-咔唑，其中Q、X、W、R1、R2、R3、R4和R5的含义如描述中所定义。本发明所述的化合物是有效的FSH拮抗剂，例如可用于男性或女性的生育控制，或预防和/或治疗骨质疏松症。
• ARYLMETHYLEN SUBSTITUTED N-ACYL-Y-AMINOALCOHOLS
  申请人：Wortmann Lars

  公开号：US20080287493A1

  公开（公告）日：2008-11-20

  The present invention relates to arylmethylen substituted N-acyl-Y-aminoalcohols of the general formula I in which Q, X, W, R1, R2, R3, R4 and R5 have the meaning as defined in the description. The compounds according to the invention are effective FSH modulators and can be used for example for fertility regulation in men or in women.

  本发明涉及一般式I的芳基亚甲基取代的N-酰基-Y-氨基醇，其中Q、X、W、R1、R2、R3、R4和R5的含义如描述中所定义。根据本发明的化合物是有效的FSH调节剂，例如可用于男性或女性的生育调节。
• Acyltryptophanols
  申请人：Wortmann Lars

  公开号：US20070060573A1

  公开（公告）日：2007-03-15

  The present patent application relates to acyltryptophanols of the general formula I, in which Q, X, Y, W, R1, R2, R3, R4, R5, R8 have the meanings stated in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

  本专利申请涉及一般式I的酰基色氨酸醇，其中Q、X、Y、W、R1、R2、R3、R4、R5、R8具有说明书中所述的含义。本发明的化合物是有效的FSH拮抗剂，例如可用于男性或女性的生育控制，或用于骨质疏松症的预防和/或治疗。