2,2,2-trifluoro-N-{1-quinolin-3-ylmethyl-3-[(2,2,2-trifluoro-acetylamino)-methyl]-pyrrolidin-3-yl}-acetamide | 871115-72-9

• 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: 2,2,2-trifluoro-N-{1-quinolin-3-ylmethyl-3-[(2,2,2-trifluoro-acetylamino)-methyl]-pyrrolidin-3-yl}-acetamide
• 英文别名: 2,2,2-trifluoro-N-[[1-(quinolin-3-ylmethyl)-3-[(2,2,2-trifluoroacetyl)amino]pyrrolidin-3-yl]methyl]acetamide
• CAS: 871115-72-9
• 化学式: C₁₉H₁₈F₆N₄O₂
• 分子量: 448.368
• InChiKey: ZGHFGYAHCRREBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  74.3
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-{1-quinolin-3-ylmethyl-3-[(2,2,2-trifluoro-acetylamino)-methyl]-pyrrolidin-3-yl}-acetamide 在 氨 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 36.0h， 生成 [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,33-trioxo-1'-(quinolin-3-ylmethyl)spiro[8,34-dioxa-24,27,30-triazapentacyclo[23.7.1.14,7.05,32.026,31]tetratriaconta-1(32),2,4,9,19,21,25,30-octaene-29,3'-pyrrolidine]-13-yl] acetate
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of a novel series of rifabutin-like spirorifamycins

  摘要：

  A novel series of spirorifamycins was synthesized and their antibacterial activity evaluated both in vitro and in vivo. This new series of rifamycins shows excellent activity against Staphylococcus aureus that is equivalent to rifabutin. However, some compounds of the series exhibit lower MICs than rifabutin against rifampin-resistant strains of S. aureus. Further, compound 2e exhibits comparable efficacy in vivo in a murine model of S. aureus septicemia model following administration by either oral or parenteral dosing routes.

  DOI：

  10.1016/j.bmcl.2006.12.026
• 作为产物：
  描述：

  3-氨基-3-氰基吡咯烷-1-羧酸叔丁酯 在 镍 吡啶 、 盐酸 、 氢气 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 反应 76.0h， 生成 2,2,2-trifluoro-N-{1-quinolin-3-ylmethyl-3-[(2,2,2-trifluoro-acetylamino)-methyl]-pyrrolidin-3-yl}-acetamide
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of a novel series of rifabutin-like spirorifamycins

  摘要：

  A novel series of spirorifamycins was synthesized and their antibacterial activity evaluated both in vitro and in vivo. This new series of rifamycins shows excellent activity against Staphylococcus aureus that is equivalent to rifabutin. However, some compounds of the series exhibit lower MICs than rifabutin against rifampin-resistant strains of S. aureus. Further, compound 2e exhibits comparable efficacy in vivo in a murine model of S. aureus septicemia model following administration by either oral or parenteral dosing routes.

  DOI：

  10.1016/j.bmcl.2006.12.026

文献信息

• Spiro-rifamycin derivatives targeting RNA polymerase
  申请人：Ma Zhenkun

  公开号：US20050277633A1

  公开（公告）日：2005-12-15

  Compounds of the current invention relate to rifamycin derivatives having antimicrobial activities, including activities against drug-resistant microorganisms. More specifically, compounds of the current invention relate to a series of novel spiro rifamycin derivatives which have demonstrated potent antimicrobial activity.

  当前发明的化合物涉及具有抗微生物活性的利福霉素衍生物，包括对耐药微生物的活性。更具体地说，当前发明的化合物涉及一系列表现出强效抗微生物活性的新型螺环利福霉素衍生物。
• US7202246B2
  申请人：——

  公开号：US7202246B2

  公开（公告）日：2007-04-10
• Synthesis and antibacterial evaluation of a novel series of rifabutin-like spirorifamycins
  作者：In Ho Kim、Keith D. Combrink、Zhenkun Ma、Katrina Chapo、Dalai Yan、Paul Renick、Timothy W. Morris、Mark Pulse、Jerry W. Simecka、Charles Z. Ding

  DOI：10.1016/j.bmcl.2006.12.026

  日期：2007.3

  A novel series of spirorifamycins was synthesized and their antibacterial activity evaluated both in vitro and in vivo. This new series of rifamycins shows excellent activity against Staphylococcus aureus that is equivalent to rifabutin. However, some compounds of the series exhibit lower MICs than rifabutin against rifampin-resistant strains of S. aureus. Further, compound 2e exhibits comparable efficacy in vivo in a murine model of S. aureus septicemia model following administration by either oral or parenteral dosing routes.