2-甲基咪唑并[1,2-a]吡啶-3-羧酸肼 | 144835-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 2-甲基咪唑并[1,2-a]吡啶-3-羧酸肼
• 英文名称: 2-methylimidazo[1,2-a]pyridine-3-carbohydrazide
• CAS: 144835-67-6
• 化学式: C₉H₁₀N₄O
• mdl: MFCD00269303
• 分子量: 190.205
• InChiKey: IOWSGEGUOPGCBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  72.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 储存条件：
  将存贮温度保持在2-8°C，并请避免光照。

反应信息

• 作为反应物：
  描述：

  2-甲基咪唑并[1,2-a]吡啶-3-羧酸肼 以43%的产率得到
  参考文献：
  名称：

  Cesur Nesrin, Cesur Zafer, Farmaco, 49 (1994) N 16, S 679-681

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基吡啶 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 23.0h， 生成 2-甲基咪唑并[1,2-a]吡啶-3-羧酸肼
  参考文献：
  名称：

  N-酰基hydr和新型构象受约束的化合物作为选择性和有效的口服活性磷酸二酯酶-4抑制剂的设计，合成和药理评价

  摘要：

  在一系列测试的N-酰基ac（NAHs）中，化合物8a被选为选择性的亚微摩尔磷酸二酯酶4（PDE4）抑制剂，与体外和体内的抗TNF-α特性相关。通过对分子模型研究阐明化合物8a的识别模式，该模型基于对zardaverine的3D结构的了解，zadaverine是一种类似于8a结构的PDE4抑制剂，与PDE4共结晶。基于对N-甲基-NAHs的进一步构象分析，喹唑啉衍生物（19）被设计为构象受限的NAH类似物，并且表现出相似的性质。体外药理学资料，与8a相比。另外，当在LPS诱发的气道高反应性中口服测试时，发现有19种有效，并且充分证实了支持这项工作的工作假设。

  DOI：

  10.1021/jm300514y

文献信息

• Microwave-assisted synthesis and photophysical studies of novel fluorescent N-acylhydrazone and semicarbazone-7-OH-coumarin dyes
  作者：Thiago Moreira Pereira、Felipe Vitório、Ronaldo Costa Amaral、Kassio Papi Silva Zanoni、Neyde Yukie Murakami Iha、Arthur Eugen Kümmerle

  DOI：10.1039/c6nj01532h

  日期：——

  microwave-assisted synthesis of novel N-acylhydrazone and semicacarbazone-7-hidroxy-coumarins derivatives, starting from 3-acetyl-7-hydroxy-2H-chromen-2-one, is described. This optimized protocol led to higher yields and considerable reduction in reaction time from ∼24 to ∼1 hour. Aqueous solutions of these compounds showed bright blue to cyan emission and maximum quantum yields of 0.244. The stereoelectronic effects

  新颖的微波辅助合成Ñ -acylhydrazone和semicacarbazone -7- hidroxy香豆素衍生物，由3-乙酰基-7-羟基-2-开始ħ -色烯-2-酮，进行说明。此优化方案可提高收率，并使反应时间从约24小时减少到约1小时。这些化合物的水溶液显示出明亮的蓝色至青色发射，最大量子产率为0.244。连接基团的立体电子效应通过偏爱顺式或反酰胺构象异构体导致光谱特性的调节。所合成的化合物显示出pH依赖的发光和在低极性介质（甲醇）强烈batochromic移位至65纳米，由于更好的稳定化的顺式-促进这种红移的合格者。这些特性可用于设计用于pH以及极性微环境的新型发光探针。
• 3-Aryl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20080045514A1

  公开（公告）日：2008-02-21

  Disclosed are 3-aryl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and analogs thereof, represented by the Formula I: wherein Ar 1 , Q 2 , R 1 , R 2 , dashed line and X are defined herein. The present invention relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及一种由公式I表示的3-芳基-6-芳基-7H-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪及其类似物，其中Ar1，Q2，R1，R2，虚线和X的定义如下。本发明发现具有公式I的化合物是caspases的激活剂和凋亡诱导剂。因此，本发明的caspases激活剂和凋亡诱导剂可用于诱导在各种临床病况中出现的异常细胞的无控制增长和扩散的细胞死亡。
• Heteroaryl-substituted triazoles as APJ receptor agonists
  申请人：AMGEN INC.

  公开号：US11046680B1

  公开（公告）日：2021-06-29

  Compounds of Formula (I) and Formula (II), pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: where the definitions of the variables are provided herein.

  式（I）和式（II）化合物、其药学上可接受的盐、前述任何化合物的立体异构体或其混合物是 APJ 受体的激动剂，可用于治疗心血管疾病和其他疾病。式 I 和式 II 的化合物具有如下结构： 其中变量的定义在本文中提供。
• Synthesis and antinociceptive properties of new structurally planned imidazo[1,2-a]pyridine 3-acylarylhydrazone derivatives
  作者：Izabella G. Ribeiro、Kelly Christine M. da Silva、Sergio C. Parrini、Ana Luisa P. de Miranda、Carlos A.M. Fraga、Eliezer J. Barreiro

  DOI：10.1016/s0223-5234(98)80012-3

  日期：1998.3

  This paper describes recent results of a research program aiming at the synthesis and pharmacological evaluation of new N-heterocyclic functionalized acylarylhydrazone compounds, belonging to 3 acyl-(2-methyl-imidazo[1,2-a]pyridinyl)-arylhydrazone 2 series. These compounds were structurally planned applying classical ring bioisosterism strategies on previously described 4-acyl-(N-phenylpyrazolyl)-arylhydrazone, which presented important analgesic properties, in order to identify the pharmacophore contribution of the acylarylhydrazone moiety and investigate the structure-activity relationship (SAR) in these series. The results herein disclosed indicate that this strategy of molecular modification gave rise to a new series of analgesic and anti-inflammatory agents, where the activity seems to be more dependent on the nature of the para-substituent at the pharmacophore acylarylhydrazone (AAH) moiety, than the N-heterocyclic acyl-ring pattern. (C) Elsevier, Paris.
• Identification and development of 2-methylimidazo[1,2-a]pyridine-3-carboxamides as Mycobacterium tuberculosis pantothenate synthetase inhibitors
  作者：Ganesh Samala、Radhika Nallangi、Parthiban Brindha Devi、Shalini Saxena、Renu Yadav、Jonnalagadda Padma Sridevi、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2014.05.038

  日期：2014.8

  In the present study, we used crystal structure of mycobacterial pantothenate synthetase (PS) bound with 2-(2-(benzofuran-2-ylsulfonylcarbamoyl)-5-methoxy-1H-indol-1-yl) acetic acid inhibitor for virtual screening of antitubercular compound database to identify new scaffolds. One of the identified lead was modified synthetically to obtain thirty novel analogues. These synthesized compounds were evaluated for Mycobacterium tuberculosis (MTB) PS inhibition study, in vitro antimycobacterial activities and cytotoxicity against RAW 264.7 cell line. Among the compounds tested, N'-(1-naphthoyl)-2-methylimidazo[1,2-a]pyridine-3-carbohydrazide (5b) was found to be the most active compound with IC₅₀ of 1.90 ± 0.12 μM against MTB PS, MIC of 4.53 μM against MTB with no cytotoxicity at 50 μM. The binding affinity of the most potent inhibitor 5b was further confirmed biophysically through differential scanning fluorimetry.