3-[4-(6-methoxyquinolinyl)]propanal | 214694-99-2

• 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: 3-[4-(6-methoxyquinolinyl)]propanal
• 英文别名: 6-Methoxy-4-quinolinepropanal；3-(6-methoxyquinolin-4-yl)propanal
• CAS: 214694-99-2
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: KIMXXRHCCKCCRL-UHFFFAOYSA-N

物化性质

• 沸点：
  371.4±27.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Erythromycin, 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-I+/--L-ribo-hexopyranosyl)oxy]-11,12-dideoxy-11,12-(hydrazonocarbonyloxy)-6-O-methyl-3-oxo- 、 3-[4-(6-methoxyquinolinyl)]propanal 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 生成 (1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-15-[3-(6-methoxyquinolin-4-yl)propylamino]-1,5,7,9,11,13-hexamethyl-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Ketolides (6-O-Methyl-3-oxoerythromycin Derivatives):  A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens

  摘要：

  In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called "ketolides". A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.

  DOI：

  10.1021/jm980240d
• 作为产物：
  描述：

  6-甲氧基-4-喹啉甲醛 在 palladium on activated charcoal 盐酸 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， -35.0~40.0 ℃ 、151.99 kPa 条件下， 反应 10.0h， 生成 3-[4-(6-methoxyquinolinyl)]propanal
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Ketolides (6-O-Methyl-3-oxoerythromycin Derivatives):  A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens

  摘要：

  In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called "ketolides". A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.

  DOI：

  10.1021/jm980240d

文献信息

• NOVEL MACROLIDE INTERMEDIATE AND NOVEL PRODUCTION PROCESS
  申请人：Meiji Seika Pharma Co., Ltd.

  公开号：EP2682399A1

  公开（公告）日：2014-01-08

  Provided are: a novel monoalkylamino intermediate (I); and a production method for a compound represented by the formula (III), which is an animal antibacterial agent, via the novel monoalkylamino intermediate.

  提供的是：一种新型的单烷基氨基中间体(I); 以及通过这种新型单烷基氨基中间体制备一种动物抗菌剂，该抗菌剂的化学式为(III)的方法。
• NOVEL 15-MEMBERED CYCLIC AZALIDE, NOVEL 16-MEMBERED CYCLIC DIAZALIDE DERIVATIVE, AND PROCESS FOR PRODUCING THESE
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：EP1479687A1

  公开（公告）日：2004-11-24

  A compound represented by the general formula (I) or a salt thereof which has excellent antibacterial activity (R1 represents hydrogen atom or an alkylcarbonyl group, R2 represents hydrogen atom, oxygen atom, hydroxyl group, or an alkylcarbonyloxy group, for example, when R2 is hydrogen atom, R3 represents group (a) (each of R5 and R6 represents hydrogen atom or an alkyl group), R4 represents hydrogen atom or group (c) (each of R8 and R9 represents hydrogen atom or an alkylcarbonyl group), and Me represents methyl group).

  通式 (I) 所代表的化合物或其盐，具有优异的抗菌活性（R1 代表氢原子或烷基羰基，R2 代表氢原子、氧原子、羟基或烷基羰氧基，例如，当 R2 为氢原子时，R3 代表 (a) 基团（R5 和 R6 各代表氢原子或烷基），R4 代表氢原子或 (c) 基团（R8 和 R9 各代表氢原子或烷基羰基），Me 代表甲基）。
• Novel 15-membered cyclic azalide, novel 16-membered cyclic diazalide derivative, and process for producing these
  申请人：Miura Tomoaki

  公开号：US20050209446A1

  公开（公告）日：2005-09-22

  A compound represented by the general formula (I) or a salt thereof which has excellent antibacterial activity (R 1 represents hydrogen atom or an alkylcarbonyl group, R 2 represents hydrogen atom, oxygen atom, hydroxyl group, or an alkylcarbonyloxy group, for example, when R 2 is hydrogen atom, R 3 represents group (a) (each of R 5 and R 6 represents hydrogen atom or an alkyl group), R 4 represents hydrogen atom or group (c) (each of R 8 and R 9 represents hydrogen atom or an alkylcarbonyl group), and Me represents methyl group).

  通式 (I) 所代表的化合物或其盐具有优异的抗菌活性（R 1 代表氢原子或烷基羰基，R 2 代表氢原子、氧原子、羟基或烷基羰氧基，例如，当 R 2 是氢原子时，R 3 代表基团 (a) （R 5 和 R 6 代表氢原子或烷基），R 4 代表氢原子或 (c) 基团（R 8 和 R 9 代表氢原子或烷基羰基），而 Me 代表甲基）。
• Synthesis and Antibacterial Activity of Ketolides (6-<i>O</i>-Methyl-3-oxoerythromycin Derivatives):  A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens
  作者：Constantin Agouridas、Alexis Denis、Jean-Michel Auger、Yannick Benedetti、Alain Bonnefoy、François Bretin、Jean-François Chantot、Arlette Dussarat、Claude Fromentin、Solange Gouin D'Ambrières、Sylvette Lachaud、Patrick Laurin、Odile Le Martret、Véronique Loyau、Nicole Tessot

  DOI：10.1021/jm980240d

  日期：1998.10.1

  In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called "ketolides". A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.