1-cyclopropyl-7-(3-ethylaminomethyl-1-pyrrolidinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride | 132065-82-8

• 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: 1-cyclopropyl-7-(3-ethylaminomethyl-1-pyrrolidinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride
• 英文别名: 1-cyclopropyl-7-[3-(ethylaminomethyl)pyrrolidin-1-yl]-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid;hydrochloride
• CAS: 132065-82-8
• 化学式: C₂₁H₂₆FN₃O₃*ClH
• 分子量: 423.915
• InChiKey: BLVSIFQUEPUPEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  72.9
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic Acid B(OCOCH3)2 Chelate 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 15.5h， 生成 1-cyclopropyl-7-(3-ethylaminomethyl-1-pyrrolidinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride
  参考文献：
  名称：

  抗菌剂的研究。三，取代的1,4-二氢-8-甲基-4-氧代喹啉-3-羧酸的合成及抗菌活性。

  摘要：

  制备一系列在8位具有甲基的取代的4-氧代喹啉-3-羧酸，并测试其抗菌活性。7-（反式-3-氨基-4-甲基-1-吡咯烷基）-1-环丙基-1,4-二氢-6-氟-8-甲基-4-氧喹啉-3-羧酸（21）表现出强效对革兰氏阳性和革兰氏阴性细菌（包括铜绿假单胞菌）均具有抗菌活性。

  DOI：

  10.1248/cpb.38.2472

文献信息

• 1-cyclopropyl-6-fluoro-8-alkyl-1,4-dihydro-4-oxo-quinoline-3-carboxylic
  申请人：Otsuka Pharmaceutical Company, Limited

  公开号：US04855292A1

  公开（公告）日：1989-08-08

  Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.6 alkyl, or a pharmaceutically acceptable salt thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.

  化合物的结构式为：##STR1##其中，R.sup.2是1-吡咯烷基，可以有1至2个取自下列组的取代基：(i) C.sub.1 -C.sub.6烷基，(ii) 氨基-(C.sub.1 -C.sub.6)烷基，该氨基可以被1或2个取自C.sub.1 -C.sub.6烷基、C.sub.1 -C.sub.6酰基和C.sub.1 -C.sub.6烷氧羰基的取代基取代，(iii) 氨基，可以被1或2个取自C.sub.1 -C.sub.6烷基、苯基(C.sub.1 -C.sub.6)烷基、C.sub.1 -C.sub.6烷氧羰基和C.sub.1 -C.sub.6酰基的取代基取代，以及(iv) 2-氧代-1,3-二氧杂环戊烷甲基氨基，该氨基被C.sub.1 -C.sub.6烷基取代；或1-哌啶基，可以有1至3个取自氧代、羟基、卤素和C.sub.1 -C.sub.6烷基的取代基，R.sup.3是C.sub.1 -C.sub.6烷基，或其药学上可接受的盐。这些化合物具有优异的抗微生物活性，因此可用作抗微生物剂，并且含有上述化合物作为活性成分的制药组合物。
• MIYAMOTO, HISASHI;UEDA, HIRAKI;OTSUKA, TATSUYA;AKI, SINJI;TAMAOKA, HISASH+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 2472-2475
  作者：MIYAMOTO, HISASHI、UEDA, HIRAKI、OTSUKA, TATSUYA、AKI, SINJI、TAMAOKA, HISASH+

  DOI：——

  日期：——
• UEDA, HIRAKI;MIYAMOTO, HISASHI;AKI, SHINIT;OTSUKA, TATSUYA
  作者：UEDA, HIRAKI、MIYAMOTO, HISASHI、AKI, SHINIT、OTSUKA, TATSUYA

  DOI：——

  日期：——
• US4855292A
  申请人：——

  公开号：US4855292A

  公开（公告）日：1989-08-08
• Studies on antibacterial agents. III. Synthesis and antibacterial activities of substituted 1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acids.
  作者：Hisashi MIYAMOTO、Hiraki UEDA、Tatsuya OTSUKA、Sinji AKI、Hisashi TAMAOKA、Michiaki TOMINAGA、Kazuyuki NAKAGAWA

  DOI：10.1248/cpb.38.2472

  日期：——

  A series of substituted 4-oxoquinoline-3-carboxylic acids having a methyl group at the 8-position was prepared and tested for their antibacterial activity. 7-(trans-3-Amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-1,4-dihydro-6- fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid (21) exhibited highly potent antibacterial activity against both gram-positive and gram-negative bacteria, including Pseudomonas

  制备一系列在8位具有甲基的取代的4-氧代喹啉-3-羧酸，并测试其抗菌活性。7-（反式-3-氨基-4-甲基-1-吡咯烷基）-1-环丙基-1,4-二氢-6-氟-8-甲基-4-氧喹啉-3-羧酸（21）表现出强效对革兰氏阳性和革兰氏阴性细菌（包括铜绿假单胞菌）均具有抗菌活性。