3-甲酰基-4,5-二甲基-1H-吡咯-2-羧酸甲酯 | 33317-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 3-甲酰基-4,5-二甲基-1H-吡咯-2-羧酸甲酯
• 英文名称: Methyl 4,5-dimethyl-3-formylpyrrole-2-carboxylate
• 英文别名: 3-formyl-4,5-dimethyl-pyrrole-2-carboxylic acid methyl ester；methyl 3-formyl-4,5-dimethylpyrrole-2-carboxylate；Methyl 3-formyl-4,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 33317-04-3
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: JRSRSELFXJTQBX-UHFFFAOYSA-N

物化性质

• 沸点：
  367.0±42.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲酰基-4,5-二甲基-1H-吡咯-2-羧酸甲酯 在 甲酸 、 水 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 35.25h， 生成 Methyl (E)-3-[N-(4-ureidophenyl)-2-carbamoylvinyl]-4,5-dimethylpyrrole-2-carboxylate
  参考文献：
  名称：

  3-(2-Carbamoylvinyl)-4,5-dimethylpyrrole-2-carboxylic acids as ligands at the NMDA glycine-binding site: a study on the 2-carbamoylvinyl chain modification

  摘要：

  Twenty 4,5-dimethylpyrrole-2-carboxylic acids (5a-t) with different 2-carbamoylvinyl chains in position 3 were prepared to further investigate the relationships between structure and in vitro affinity for the strychnine-insensitive glycine-binding site. None of these compounds was superior to (E)-3-(N-phenyl-2-carbamoylvinyl)-4,5-dimethylpyrrole-2-carb oxylic acid III (pKi = 6.70), which was taken as a reference standard, but overall the results obtained indicate that the N-phenyl-2-carbamoylvinyl substituent of III may be replaced with the N-(1-adamantyl)-2-carbamoylvinyl group as in 5h (pKi = 6.20) without considerable loss of affinity. This finding adds to previous knowledge.

  DOI：

  10.1016/s0014-827x(98)00110-4
• 作为产物：
  描述：

  4,5-二甲基-2-吡咯羧酸甲酯 在 sodium hydroxide 、 三氯氧磷 作用下， 以 N-甲基乙酰胺 、 正己烷 、 乙酸乙酯 为溶剂， 生成 3-甲酰基-4,5-二甲基-1H-吡咯-2-羧酸甲酯
  参考文献：
  名称：

  US6063782

  摘要：

  公开号：

文献信息

• (<i>E</i>)-3-(2-(<i>N</i>-Phenylcarbamoyl)vinyl)pyrrole-2-carboxylic Acid Derivatives. A Novel Class of Glycine Site Antagonists
  作者：Cesarino Balsamini、Annalida Bedini、Giuseppe Diamantini、Gilberto Spadoni、Andrea Tontini、Giorgio Tarzia、Romano Di Fabio、Aldo Feriani、Angelo Reggiani、Giovanna Tedesco、Roberta Valigi

  DOI：10.1021/jm970416w

  日期：1998.3.1

  biological evaluation of novel (E)-3-(2-(N-phenylcarbamoyl)-vinyl)pyrrole-2-carboxylic acids bearing alkyl, acyl, alkoxy, phenyl, and halo substituents at the 4- and 5-positions of the pyrrole ring are reported. These compounds were studied for their in vitro affinity at the strychnine-insensitive glycine-binding site of the N-methyl-D-aspartate (NMDA) receptor complex. In the [3H]glycine binding assay (E)-4

  新型（E）-3-（2-（N-苯基氨基甲酰基）-乙烯基）吡咯-2-羧酸在4-和5-上带有烷基，酰基，烷氧基，苯基和卤素取代基的合成及初步生物学评价报告了吡咯环的位置。研究了这些化合物在N-甲基-D-天冬氨酸（NMDA）受体复合物的对苯丙氨酸不敏感的甘氨酸结合位点的体外亲和力。在[3H]甘氨酸结合测定中，（E）-4,5-二溴-3-（2-（N-苯基氨基甲酰基）乙烯基）吡咯-2-羧酸6w（pKi = 7.95 +/- 0.01）和4-溴5-甲基6j（pKi = 7.24 +/- 0.01）和4,5-二甲基6g（pKi = 6.70 +/- 0.03）类似物是该系列中活性最高的化合物。定性结构活性分析指出C-4和C-5取代基的体积与亲和力之间呈负相关，而卤素取代基增强了亲和力。通过Hansch描述符F，R，pi和MR对pKi>或= 4的化合物子集进行的QSAR分析表明，C-4和C-5处的吸电子基团增
• Optically active pyrrolopyridazine derivatives
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20020156079A1

  公开（公告）日：2002-10-24

  An optically active pyrrolopyridazine compound of the formula (I) or a pharmaceutically acceptable salt thereof: 1 wherein R 1 is alkyl; R 2 and R 3 are each independently alkyl; R 4 is optionally substituted aryl; and A is imino, oxygen or sulfur. The pyrrolopyridazine compound or pharmaceutically acceptable salts thereof of the present invention exhibit excellent gastric acid secretory inhibition activity and gastric mucous membrane protection activity, as well as excellent antibacterial activity against Helicobacter pylori. They are useful medicines and are particularly useful for treating or preventing ulcerative diseases.

  式(I)的旋光异构的吡咯吡啶嗪化合物或其药学上可接受的盐： 其中R1是烷基；R2和R3各自独立地是烷基；R4是可选取代的芳基；A是亚胺基、氧原子或硫原子。本发明的吡咯吡啶嗪化合物或其药学上可接受的盐，表现出优异的胃酸分泌抑制活性和胃粘膜保护活性，以及对幽门螺杆菌的优异抗菌活性。它们是有用的药物，特别是用于治疗或预防溃疡性疾病。
• Pyrrolopyridazine compounds
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20040014762A1

  公开（公告）日：2004-01-22

  A pyrrolopyridazine compound having the formula (I) or a pharmaceutically acceptable salt thereof: 1 wherein, R 1 is a C 2 -C 6 alkenyl group, a halogeno C 2 -C 6 alkenyl group, a C 3 -C 7 cycloalkyl group which may be optionally substituted or a C 3 -C 7 cycloalkyl- C 1 -C 6 alkyl group which may be optionally substituted. R 2 is a C 1 -C 6 alkyl group. R 3 is a hydroxymethyl group, a C 2 -C 6 aliphatic acyloxymethyl group, a C 6 -C 10 arylcarbonyloxymethyl group which may be optionally substituted, a C 1 -C 6 alkoxycarbonyloxymethyl group, a formyl group, a carboxyl group, a C 1 -C 6 alkoxycarbonyl group or a C 6 -C 10 aryloxycarbonyl group which may be optionally substituted. R 4 is a C 6 -C 10 aryl group which may be optionally substituted. A is an imino group, an oxygen atom or a sulfur atom. These compounds exhibit excellent gastric acid secretory inhibition activity and gastric mucous membrane protection activity etc. They are useful for prevention or treatment of ulcerative diseases and for Helicobacter pylori infections.

  一种具有以下式(I)或其药学上可接受的盐的吡咯吡啶化合物： 1其中，R1是C2-C6烯丙基，卤代C2-C6烯丙基，C3-C7环烷基，其可以选择性地取代或C3-C7环烷基-C1-C6烷基，其可以选择性地取代。R2是C1-C6烷基。R3是羟甲基，C2-C6脂肪酰氧甲基，C6-C10芳基羰基氧甲基，其可以选择性地取代，C1-C6烷氧羰基氧甲基，甲酰基，羧基，C1-C6烷氧羰基或C6-C10芳氧羰基，其可以选择性地取代。R4是C6-C10芳基，其可以选择性地取代。A是亚胺基，氧原子或硫原子。这些化合物表现出优异的胃酸分泌抑制活性和胃黏膜保护活性等。它们对于预防或治疗溃疡性疾病和幽门螺杆菌感染非常有用。
• PYRROLOPYRIDAZINE DERIVATIVE
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0742218A1

  公开（公告）日：1996-11-13

  Pyrrolopyridazine derivatives having the general formula. [In the above formula, R1 represents a C2-C6 alkenyl group, a halogeno-C2-C6-alkenyl group, a C6-C10 aryl-C2-C6-alkenyl group, a C2-C6 alkynyl group, a C3-C7 cycloalkyl group, a C3-C7 cycloalkyl-C1-C6-alkyl group, a C5-C7 cycloalkenyl-C1-C6-alkyl group or a halogeno-C1-C6-alkyl group; R2 and R3 are the same or different and each represents a hydrogen atom, a C1-C6 alkyl group or a C6-C10 aryl group; R4 represents a hydrogen atom or a C1-C6 alkyl group; R5 represents a C6-C10 aryl group or a 5-10 membered heteroaryl group comtaining heteroatom(s) selected from nitrogen, oxygen and sulfur; A represents a C1-C3 alkylene group; X represents an imino group, an oxygen atom, a sulfur atom or a methylene group; m represents 0 or 1; and n represents 0 or 1] or pharmaceutically acceptable salts thereof. [Effect] The pyrrolopyridazine derivatives of the present invention have an excellent gastric secretion inhibiting activity, gastric mucosa protective activity and antibacterial activity against Helicobacter pylori, and are useful as a preventive or therapeutic agent for ulcerous diseases.

  具有通式的吡咯哒嗪衍生物。 [在上式中，R1 代表 C2-C6 烯基、卤代-C2-C6-烯基、C6-C10 芳基-C2-C6-烯基、C2-C6 炔基、C3-C7 环烷基、C3-C7 环烷基-C1-C6-烷基、C5-C7 环烯基-C1-C6-烷基或卤代-C1-C6-烷基；R2 和 R3 相同或不同，各自代表氢原子、C1-C6 烷基或 C6-C10 芳基；R4 代表氢原子或 C1-C6 烷基；R5 代表 C6-C10 芳基或含有选自氮、氧和硫的杂原子的 5-10 位杂芳基； A代表C1-C3亚烷基；X代表亚氨基、氧原子、硫原子或亚甲基；m代表0或1；n代表0或1]。 或其药学上可接受的盐类。 效果 本发明的吡咯哒嗪衍生物具有良好的胃分泌抑制活性、胃黏膜保护活性和幽门螺旋杆菌抗菌活性，可作为溃疡病的预防或治疗剂。
• OPTICALLY ACTIVE PYRROLOPYRIDAZINE COMPOUNDS
  申请人：Sankyo Company, Limited

  公开号：EP1186607B1

  公开（公告）日：2003-05-21