2-(pyridin-3-yl)thiazole-5-carbaldehyde | 882032-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(pyridin-3-yl)thiazole-5-carbaldehyde
• 英文别名: 2-(Pyridin-3-yl)-1,3-thiazole-5-carbaldehyde；2-pyridin-3-yl-1,3-thiazole-5-carbaldehyde
• CAS: 882032-77-1
• 化学式: C₉H₆N₂OS
• mdl: MFCD11846890
• 分子量: 190.225
• InChiKey: ZNLXETCAQSWLSS-UHFFFAOYSA-N

物化性质

• 沸点：
  387.9±48.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(pyridin-3-yl)thiazole-5-carbaldehyde 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 N1-methyl-N1-((2-(pyridin-3-yl)-1,3-thiazol-5-yl)methyl)ethane-1,2-diamine
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel C₁₂ Vinyl Ketolides

  摘要：

  A novel series Of C-12 vinyl erythromycin derivatives have been discovered which exhibit in vitro and in vivo potency against key respiratory pathogens. The C-12 modification involves replacing the natural C-12 methyl group in the erythromycin core with a vinyl group via chemical synthesis. From the C-12 vinyl macrolide core, a series Of C-12 vinyl ketolides was prepared. Several compounds were found to be potent against macrolide-sensitive and -resistant bacteria. The C-12 vinyl ketolides 6j and 6k showed a similar antimicrobial spectrum and comparable activity to the commercial ketolide telithromycin. However, the pharmacokinetic profiles Of C-12 vinyl ketolides 6j and 6k in rats differ from that of telithromycin by having higher lung-to-plasma ratios, larger volumes of distribution, and longer half-lives. These pharmacokinetic differences have a pharmacodynamic effect as both 6j and 6k exhibited better in vivo efficacy than telithromycin in rat lung infection models against Streptococcus pneumoniae and Haemophilus influenzae.

  DOI：

  10.1021/jm051157a
• 作为产物：
  描述：

  二乙基(3-吡啶基)-硼烷 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 67.0h， 生成 2-(pyridin-3-yl)thiazole-5-carbaldehyde
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel C₁₂ Vinyl Ketolides

  摘要：

  A novel series Of C-12 vinyl erythromycin derivatives have been discovered which exhibit in vitro and in vivo potency against key respiratory pathogens. The C-12 modification involves replacing the natural C-12 methyl group in the erythromycin core with a vinyl group via chemical synthesis. From the C-12 vinyl macrolide core, a series Of C-12 vinyl ketolides was prepared. Several compounds were found to be potent against macrolide-sensitive and -resistant bacteria. The C-12 vinyl ketolides 6j and 6k showed a similar antimicrobial spectrum and comparable activity to the commercial ketolide telithromycin. However, the pharmacokinetic profiles Of C-12 vinyl ketolides 6j and 6k in rats differ from that of telithromycin by having higher lung-to-plasma ratios, larger volumes of distribution, and longer half-lives. These pharmacokinetic differences have a pharmacodynamic effect as both 6j and 6k exhibited better in vivo efficacy than telithromycin in rat lung infection models against Streptococcus pneumoniae and Haemophilus influenzae.

  DOI：

  10.1021/jm051157a

文献信息

• Structure activity relationship of N-1 substituted 1,5-naphthyrid-2-one analogs of oxabicyclooctane-linked novel bacterial topoisomerase inhibitors as broad-spectrum antibacterial agents (Part-9)
  作者：Sheo B. Singh、Christopher M. Tan、David Kaelin、Peter T. Meinke、Lynn Miesel、David B. Olsen、Hideyuki Fukuda、Ryuta Kishii、Masaya Takei、Kohei Ohata、Tomoko Takeuchi、Taku Shibue、Hisashi Takano、Akinori Nishimura、Yasumichi Fukuda

  DOI：10.1016/j.bmcl.2022.128808

  日期：2022.11

  Novel bacterial topoisomerase inhibitors (NBTIs) are the newest members of gyrase inhibitor broad-spectrum antibacterial agents, represented by the most advanced member, gepotidacin, a 4-amino-piperidine linked NBTI, which is undergoing phase III clinical trials for treatment of urinary tract infections (UTI). We have extensively reported studies on oxabicyclooctane linked NBTIs, including AM-8722

  新型细菌拓扑异构酶抑制剂（NBTI）是旋转酶抑制剂广谱抗菌药的最新成员，以最先进的成员吉泊达星（4-氨基哌啶连接的NBTI）为代表，目前正在进行治疗尿路感染的Ⅲ期临床试验。感染（尿路感染）。我们广泛报道了有关氧杂双环辛烷连接的 NBTI 的研究，包括 AM-8722。本研究总结了 AM-8722 的结构活性关系 (SAR)，从而鉴定了基于 7-氟-1-氰甲基-1,5-萘啶-2-酮的 NBTI（16，AM-8888），其效力和谱图得到了改进（ MIC 值为 0.016–4 μg/mL），铜绿假单胞菌是最不敏感的菌株（MIC 4 μg/mL）。
• WO2021062318A5
  申请人：——

  公开号：WO2021062318A5

  公开（公告）日：2023-08-22
• Neue Amide als Schädlingsbekämpfungsmittel
  申请人：Bayer CropScience AG

  公开号：EP2725022B1

  公开（公告）日：2017-03-29
• THIAZOLE CARBOXAMIDE COMPOUNDS AND USE THEREOF FOR THE TREATMENT OF MYCOBACTERIAL INFECTIONS
  申请人：THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT, INC.

  公开号：US20220396586A1

  公开（公告）日：2022-12-15

  Provided herein are compounds of Formula (I) and Formula (II) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of tuberculosis.
• [EN] THIAZOLE CARBOXAMIDE COMPOUNDS AND USE THEREOF FOR THE TREATMENT OF MYCOBACTERIAL INFECTIONS<br/>[FR] COMPOSÉS DE THIAZOLE CARBOXAMIDE ET LEUR UTILISATION POUR LE TRAITEMENT D'INFECTIONS MYCOBACTÉRIENNES
  申请人：THE GLOBAL ALLIANCE FOR TB DRUG DEV INC

  公开号：WO2021062318A1

  公开（公告）日：2021-04-01

  Provided herein are compounds of Formula (I) and Formula (II) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of tuberculosis.