methyl thiophene-2-carboximidate | 54610-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: methyl thiophene-2-carboximidate
• 英文别名: methyl 2-thiophene carboximidate；Methyl 2-thiophenecarboximidate
• CAS: 54610-60-5
• 化学式: C₆H₇NOS
• 分子量: 141.194
• InChiKey: XNOKHLOMKSJULZ-UHFFFAOYSA-N

物化性质

• 沸点：
  176.3±32.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl thiophene-2-carboximidate 在 sodium methylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 4,5-dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-2-(thien-2-yl)-1,3-oxazole
  参考文献：
  名称：

  Phenylephrine derivatives as leukotriene D4 antagonists

  摘要：

  Two series of phenylephrine derivatives were prepared and tested as inhibitors of leukotriene D4 (LTD4) induced and ovalbumin-induced bronchospasm in the guinea pig. The most potent compound of the urea series, (R)-N,N-diethyl-N-[2-hydroxy-2-[3-(2-quinolinylmethoxy)phenyl]ethyl]-N- methylurea (3, Wy-47,120), was orally active with ED50's of 56 mg/kg vs. LTD4 and 55 mg/kg vs. ovalbumin. When tested as an antagonist of LTD4-induced contraction of isolated guinea pig tracheal strips, 3 was a competitive inhibitor with a p kappa B value of 5.22. In the second series, (R)-3-methyl-5-[3-(2-quinolinylmethoxy)phenyl]-2-oxazolidinone (26, Wy-47,674) had oral ED50's of 36 mg/kg against LTD4 and 95 mg/kg against ovalbumin. Compound 26 selectively antagonized contractile responses of guinea pig trachea evoked by LTD4 (p kappa B = 6.09). In the cat coronary artery, 3 dilated the preparation and blocked the coronary constrictor effect of LTD4. Compound 3 (0.13 mg/kg, iv) also preserved myocardial integrity in rats 48 h after coronary artery ligation. When tested in the rat alcohol-induced gastric lesion model, 3 and 26 manifested a dose-dependent mucosal protection against ethanol.

  DOI：

  10.1021/jm00394a026
• 作为产物：
  描述：

  2-氰基噻吩 在 盐酸 、 碳酸氢钠 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 methyl thiophene-2-carboximidate
  参考文献：
  名称：

  新型 2,3-二氢-1,3,5,4-噻二氮杂磷衍生物的高效合成

  摘要：

  摘要各种缩氨基硫脲与甲基噻吩-2-甲酰亚胺酯缩合得到相应的中间体2a-2h。后一种化合物与六甲基磷三酰胺的后续环化构成了合成新型高度官能化硫二氮杂磷衍生物 4a-4h 的新途径。该方法具有显着的优势，例如效率高、产率高和反应条件温和。图形概要

  DOI：

  10.1080/17415993.2016.1163698

文献信息

• Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them
  申请人：Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)

  公开号：US06335445B1

  公开（公告）日：2002-01-01

  A compound selected from the group consisting of a compound of the formula wherein A is selected from the group consisting of and the other substituents are defined in the specification having an inhibitory activity of NO-synthase enzymes producing nitrogen mono-oxide and/or an activity which traps the reactive oxygen species.

  从以下化合物组中选择的一种化合物，其化学式为 其中A是从以下组中选择的 其他取代基在规范中定义，具有抑制NO合酶产生一氧化氮的活性和/或捕获活性氧化物种的活性。
• Carboximidamide derivatives
  申请人：Kirin Beer Kabushiki Kaisha

  公开号：US05166347A1

  公开（公告）日：1992-11-24

  Novel carboximidamide derivatives represented by the following formula (A) and acid adduct salts thereof are disclosed: ##STR1## wherein all the substituents have the same meanings as defined above. N-cyano-pyridinecarboximidate compounds represented by the following formula (II) which are the intermediates for preparing of N-cyano-N'-substituted-pyridinecarboximidamide derivatives wherein the substituent B in the above described formula (A) is pyridine is also disclosed: ##STR2## wherein all the substitutents have the same meanings as defined above. The process for preparing the compounds, the pharmaceutical agents comprising the compound having vasodilating effect, and the therapeutic method of dosing the compound on patients for therapy are also disclosed.

  揭示了由以下公式（A）代表的新型羧酸脒衍生物及其酸加合物盐：##STR1## 其中所有取代基的含义与上文定义的相同。也揭示了由以下公式（II）代表的N-氰基吡啶羧酰脒化合物，这些化合物是制备N-氰基-N'-取代吡啶羧酰脒衍生物的中间体，在上述公式（A）中描述的取代基B为吡啶：##STR2## 其中所有取代基的含义与上文定义的相同。还揭示了制备这些化合物的方法，包含具有扩血管作用的化合物的药物剂，以及在患者身上治疗的治疗方法。
• Alkali α-MnO₂/Na_xMnO₂ collaboratively catalyzed ammoxidation–Pinner tandem reaction of aldehydes
  作者：Xiuquan Jia、Jiping Ma、Min Wang、Xiaofang Li、Jin Gao、Jie Xu

  DOI：10.1039/c6cy00874g

  日期：——

  while the potassium cation promotes the formation of a redox-active α-MnO2 phase. The interface structure of α-MnO2/NaxMnO2 geometrically favors the ammoxidation–Pinner tandem reaction to synthesize imidates in a 58–96% yield from aldehydes. Thus a phase collaborative effect is observed. In the ammoxidation process, the redox cycle of MnIV/MnIII is involved and the lattice oxygen in the α-MnO2 phase acts

  串联反应是一个不断发展的领域，可以向绿色和可持续化学领域取得重要进展。在本文中，我们报道了双功能锰氧化物催化剂与接口结合的氧化还原相（α-MnO的2）和一个基本相（钠X的MnO 2）。的NaOH / Mn的摩尔比起着α-MnO的形成了极大的作用2 /钠X的MnO 2。钠阳离子为基本的Na的形成是必需的X的MnO 2，而钾阳离子促进氧化还原活性α-MnO的形成相2相。所述的接口结构的α的MnO 2 /钠X的MnO 2从几何学上讲，它有利于氨氧化-PIN串联反应以醛的形式合成酰亚胺，产率为58-96％。因此，观察到阶段协作效应。在氨氧化反应过程中，Mn的氧化还原循环IV / Mn为III是参与并在α-MnO的晶格氧2相作为活性氧种。甲醇中的OH被活化，并在Na x MnO 2的碱性位点上解离成吸附的甲氧基，从而促进Pinner合成。该方法绕过了酰亚胺合成的常规方法，该方法面临苛刻的反应条件和需要多个步骤。
• A simple and convenient one-pot method for the preparation of heteroaryl-2-imidazoles from nitriles
  作者：Matthew E. Voss、Catherine M. Beer、Scott A. Mitchell、Peter A. Blomgren、Paul E. Zhichkin

  DOI：10.1016/j.tet.2007.11.009

  日期：2008.1

  A simple, convenient and high-yielding one-pot method for the synthesis of 2-heterocycle-substituted imidazoles from the corresponding nitriles has been developed. The procedure is easily scaleable and the workup does not involve chromatography. This synthesis is also applicable to the preparation of imidazoles with electron-poor aryl substituents.

  已经开发了一种简单，方便且高产率的一锅法，用于从相应的腈中合成2-杂环取代的咪唑。该过程易于规模化，并且后处理不涉及色谱法。该合成方法也可用于制备具有贫电子芳基取代基的咪唑。
• Cyanomidines. I. Synthesis and Vasodilatory Activity of N-Substituted Heteroaromatic Cyanoamidines.
  作者：Tatsuo NAKAJIMA、Toshio IZAWA、Tomoko KASHIWABARA、Shohachi NAKAJIMA、Yuuji MUNEZUKA

  DOI：10.1248/cpb.42.2475

  日期：——

  Various heteroaromatic cyanoamidines were synthesized starting from nitriles via cyanoimidates or from amides via thioamides. The compounds were tested for inhibitory effect on the 40 mM K+-induced contraction of rat aorta strips and selected compounds were also evaluated for antagonism of the norepinephrine-induced contraction. Most of the cyanoamidines showed vasodilatory activities. Potent vasoactive compounds were also examined for stimulation of the 86Rb+ efflux to determine their potassium channel opening actions. Maximum potency was displayed by N-cyano-N'-(2-nitroxyethyl)-3-pyridinecarboxyamidine (3h). The methanesulfonate of 3h, which was designated as KRN2391, has been selected for further development as an antianginal agent.

  各种异芳香氰基脲被合成，起始材料为腈，经过氰基咪唑或从酰胺经过硫酰胺。对这些化合物进行了抑制实验，以测试它们对40 mM K+诱导的大鼠主动脉条收缩的影响，同时还评估了选定化合物对去甲肾上腺素诱导的收缩的拮抗作用。大多数氰基脲表现出血管扩张活性。还对强效血管活性化合物进行了86Rb+外流的刺激实验，以确定它们的钾通道开放作用。N-氰基-N'-(2-硝氧基乙基)-3-吡啶羧基脲（3h）显示出最大的效力。3h的甲烷磺酸盐，命名为KRN2391，被选中进一步开发作为抗心绞痛药物。