4-(methoxyimino)piperidine | 109383-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(methoxyimino)piperidine
• 英文别名: N-methoxypiperidine-4-imine；piperidin-4-one O-methyl-oxime；piperidin-4-on-O-methyloxime；N-methoxypiperidin-4-imine
• CAS: 109383-63-3
• 化学式: C₆H₁₂N₂O
• mdl: MFCD13178775
• 分子量: 128.174
• InChiKey: GRXVKHFAPSGQDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  193.7±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(methoxyimino)piperidine 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(2-aminoethyl)-4-methoxyazanylidenepiperidine
  参考文献：
  名称：

  含有2,4-二甲基-1H-吡咯-3-甲酰胺基的5-Bromo-7-氮杂吲哚-2-one衍生物的合成及抗肿瘤活性。

  摘要：

  我们在这里报告了设计和合成的一系列新型的5-溴-7-氮杂吲哚-2-酮衍生物，其中含有2，4-二甲基-1H-吡咯-3-羧酰胺部分。通过MTT分析评估了这些新合成的衍生物对所选癌细胞系的体外活性。结果表明，某些化合物具有广谱抗肿瘤功效，并且发现活性最高的化合物23p（IC50：2.357-3.012μM）比舒尼替尼（IC50：31.594-49.036μM）对HepG2，A549和Skov-3的效力更高。 。

  DOI：

  10.3390/molecules21121674
• 作为产物：
  描述：

  4-Piperidinone O-methyloxime hydrochloride 生成 4-(methoxyimino)piperidine
  参考文献：
  名称：

  BALDWIN, JOHN J.;TOLMAN, RICHARD L.;WU, MU T.

  摘要：

  DOI：

文献信息

• [EN] CYCLOHEXENE DERIVATIVE, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING METABOLIC DISEASE COMPRISING THE SAME AS ACTIVE INGREDIENT<br/>[FR] DÉRIVÉ DE CYCLOHEXÈNE, SON PROCÉDÉ DE PRÉPARATION ET COMPOSITION PHARMACEUTIQUE POUR PRÉVENIR OU TRAITER UNE MALADIE MÉTABOLIQUE, CONTENANT LEDIT DÉRIVÉ COMME PRINCIPE ACTIF
  申请人：HYUNDAI PHARM CO LTD

  公开号：WO2017078352A1

  公开（公告）日：2017-05-11

  The present invention relates to: a cyclohexene derivative; a preparation method thereof; and a pharmaceutical composition for preventing or treating metabolic disease comprising the same as an active ingredient. The cyclohexene derivative according to the present invention increases the intracellular activity of cyclic adenosine monophosphate (cAMP) by activating G protein-coupled receptor 119 (GPR-119) and simultaneously exhibits weight loss and hypoglycemic effects by inducing the release of glucagon-like peptide-1 (GLP-1), which is a neuroendocrine protein, and thus can be useful as a pharmaceutical composition for preventing or treating metabolic diseases such as obesity, type 1 diabetes, type 2 diabetes, inadequate glucose tolerance, insulin resistance, hyperglycemia, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, dyslipidemia and syndrome X.

  本发明涉及：一种环己烯衍生物；其制备方法；以及一种包含该衍生物作为活性成分的用于预防或治疗代谢疾病的药物组合物。根据本发明的环己烯衍生物通过激活G蛋白偶联受体119（GPR-119）增加了细胞内环状腺苷一磷酸（cAMP）的活性，并通过诱导释放神经内分泌蛋白胰高血糖素样肽-1（GLP-1），同时表现出减肥和降糖效果，因此可作为预防或治疗诸如肥胖、1型糖尿病、2型糖尿病、葡萄糖耐量不足、胰岛素抵抗、高血糖、高脂血症、高甘油三酯血症、高胆固醇血症、血脂异常和综合征X等代谢疾病的药物组合物。
• [EN] IMIDAZOPYRAZINE SYK INHIBITORS<br/>[FR] INHIBITEURS IMIDAZOPYRAZINE DE LA SYK
  申请人：GILEAD CONNECTICUT INC

  公开号：WO2013188856A1

  公开（公告）日：2013-12-19

  Certain imidazopyrazines and pharmaceutical compositions thereof are provided herein. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of Syk activity, which comprises administering to such patients an amount of an imidazopyrazine compound effective to reduce signs or symptoms of the disease or disorder are provided.

  本发明提供了某些咪唑并吡唑化合物及其药物组合物。还提供了治疗患有某些对Syk活性抑制有响应的疾病和障碍的患者的方法，该方法包括向这样的患者施用足以减少疾病或障碍的症状或体征的咪唑并吡唑化合物。
• Synthesis, evaluation and CoMFA/CoMSIA study of nitrofuranyl methyl N-heterocycles as novel antitubercular agents
  作者：Apeng Wang、Yang Yang、Yangsheng Jun、Bin Wang、Kai Lv、Mingliang Liu、Huiyuan Guo、Yu Lu

  DOI：10.1016/j.bmc.2018.03.004

  日期：2018.5

  chemical series employing comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) techniques. The developed CoMFA and CoMSIA models display high external predictability (r2pred of 0.954 and 0.935, respectively) and good statistical robustness. More importantly, the newly designed compounds 16a and 16b (MIC: <0.016 μg/mL) based on the two models, as expected

  设计并合成了一系列基于IIIM-MCD-211结构的新型硝基呋喃基甲基N-杂环。化合物6d，8b和12a对MTB H37Rv菌株表现出优异的活性（MIC：0.031–0.062μg/ mL），与INH和IIIM-MCD-211大致相当。此外，利用比较分子场分析（CoMFA）和比较分子相似性指数分析（CoMSIA）技术对上述化学系列进行了三维定量构效关系（3D-QSAR）研究。已开发的CoMFA和CoMSIA模型显示出较高的外部可预测性（r 2 pred分别为0.954和0.935）和良好的统计稳健性。更重要的是，如预期的那样，发现基于两种模型的新设计的化合物16a和16b（MIC：<0.016μg/ mL）比12a和IIIM-MCD-21更具活性。目前正在进行更有效的硝基呋喃基甲基N-杂环化合物作为抗结核病药物的设计和合成。
• Design, synthesis and evaluation of oxime-functionalized nitrofuranylamides as novel antitubercular agents
  作者：Yi-Lei Fan、Jian-Bing Wu、Xing Ke、Zhong-Ping Huang

  DOI：10.1016/j.bmcl.2018.07.046

  日期：2018.10

  H37Rv and drug-resistant clinical isolates. Among them, two compounds 7a and 7b exhibited excellent activity against the three tested strains. Both of them were comparable to the first-line anti-TB agents INH and RIF against MTB H37Rv, and were far more potent than INH and RIF against MDR-TB 16833 and 16995 strains. Thus, both of them could act as leads for further optimization.

  设计，合成了一系列肟官能化的硝基呋喃酰胺，并评估了它们对MTB H37Rv和耐药临床分离株的体外抗分枝杆菌活性。其中，两种化合物7a和7b对三种测试菌株表现出优异的活性。它们两者均与针对MTB H37Rv的一线抗结核病药物INH和RIF相当，并且比针对MDR-TB 16833和16995菌株的INH和RIF更有力。因此，它们两者都可以作为进一步优化的线索。
• TETRAHYDROQUINOXALINE UREA DERIVATIVES, PREPARATION THEREOF, AND THERAPEUTIC USE THEREOF
  申请人：Namane Claudie

  公开号：US20120135958A1

  公开（公告）日：2012-05-31

  The invention relates to compounds of formula (I), where: A is a bond, an oxygen, or an —CH 2 — group; Ar 1 is a phenyl or heteroaryl group; Ar 2 is a phenyl, heteroaryl, or heterocycloalkyl group; R 1a,b,c and R 2a,b,c are hydrogen or halogen, or an alkyl, cycloalkyl, or lkyl-cycloalkyl group optionally, substituted by one or more halogen atoms, or a —OR 5 (hydroxy or alkoxy), hydroxy-alkyl, alkoxy-alkyl, alkoxy-alkoxy, halogenoalkyl, —O-halogenoalkyl, oxo, —CO-alkyl, —CO-alkyl-NR 6 R 7 , —CO-halogenoalkyl, —COOR 5 , alkyl-COOR 5 , —O-alkyl-COOR 5 , —SO 2 -alkyl, —SO 2 -cycloalkyl, —SO 2 -alkyl-cycloalkyl, —SO 2 -alkyl-OR 5 , —SO 2 -alkyl-COOR 5 , —SO 2 -alkyl-NR 6 R 7 , —SO 2 -halogenoalkyl, alkyl-SO 2 -alkyl, —SO 2 —NR 6 R 7 , —SO 2 -alkyl-O-alkyl-OR 5 , —CONR 6 R 7 , -alkyl-CONR 6 R 7 , or -alkyl-NR 6 R 7 group, or further R 1a , R 1b , and R 1c are bonded to R 2a , R 2b , R 2c , respectively, and to the carbon atom having same, and are -alkyl-O—; R 3 is a hydrogen atom or an alkyl group; R 4 is a hydrogen or halogen atom or a cyano, —OR 5 , hydroxyalkyl, —COOR 5 , —NR 6 R 7 , ONR 6 R 7 , —SO 2 -alkyl, SO 2 —NR 6 R 7 , —NR 6 —COOR 5 , —NR 6 —COR 5 , or —CO—NR 6 -alkyl-OR 5 group; R 5 , R 6 , and R 7 are a hydrogen, or an alkyl or alkyl-phenyl group; and R 8 is an alkyl, alkyl-Si(alkyl) 3 , —SO 2 -alkyl-Si(alkyl) 3 , phenyl, alkoxy-imino group, or alkyl-cycloalkyl group optionally substituted by one or more halogen atoms or one or more hydroxyl or hydroxyl-alkyl groups; or R 8 and R 9 , together with the carbon atoms to which they are bonded, form a cycloalkyl group optionally substituted by one or more halogen atoms or one or more carboxy groups; and R 9 is a hydrogen atom or an alkyl group; with the proviso that, when R 8 is an alkyl group, it is bonded onto the Ar 2 silicon atom. The invention also relates to a method for preparing same and to the therapeutic use thereof.

  该发明涉及公式(I)的化合物，其中：A是一个键，一个氧或一个—CH2—基团；Ar1是一个苯基或杂环芳基；Ar2是一个苯基，杂环芳基或杂环烷基基团；R1a，b，c和R2a，b，c是氢或卤素，或一个烷基，环烷基或烷基-环烷基基团，可以被一个或多个卤素原子取代，或一个—OR5（羟基或烷氧基），羟基-烷基，烷氧基-烷基，烷氧基-烷氧基，卤代烷基，—O-卤代烷基，酮基，—CO-烷基，—CO-烷基-NR6R7，—CO-卤代烷基，—COOR5，烷基-COOR5，—O-烷基-COOR5，—SO2-烷基，—SO2-环烷基，—SO2-烷基-环烷基，—SO2-烷基-OR5，—SO2-烷基-COOR5，—SO2-烷基-NR6R7，—SO2-卤代烷基，烷基-SO2-烷基，—SO2-NR6R7，—SO2-烷基-O-烷基-OR5，—CONR6R7，-烷基-CONR6R7，或-烷基-NR6R7基团，或进一步的R1a，R1b和R1c与R2a，R2b和R2c分别结合，并与具有相同的碳原子结合，并且是-烷基-O-；R3是氢原子或烷基基团；R4是氢或卤素原子或氰基，—OR5，羟基烷基，—COOR5，—NR6R7，ONR6R7，—SO2-烷基，SO2-NR6R7，—NR6—COOR5，—NR6—COR5，或—CO—NR6-烷基-OR5基团；R5，R6和R7是氢，或烷基或烷基-苯基基团；R8是一个烷基，烷基-Si（烷基）3，—SO2-烷基-Si（烷基）3，苯基，烷氧基-亚胺基团，或烷基-环烷基基团，可以被一个或多个卤素原子或一个或多个羟基或羟基-烷基基团取代；或R8和R9，与它们结合的碳原子一起，形成一个可以被一个或多个卤素原子或一个或多个羧基取代的环烷基基团；R9是氢原子或烷基基团；但是，当R8是烷基基团时，它与Ar2硅原子结合。该发明还涉及制备该化合物的方法和其治疗用途。