Methyl 5-bromofuran-3-carboxylate | 197846-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: Methyl 5-bromofuran-3-carboxylate
• CAS: 197846-08-5
• 化学式: C₆H₅BrO₃
• 分子量: 205.008
• InChiKey: DDCVXKKLSQNHIK-UHFFFAOYSA-N

物化性质

• 沸点：
  208.7±20.0 °C(Predicted)
• 密度：
  1.623±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 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：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 5-bromofuran-3-carboxylate 在 potassium phosphate 、 草酰氯 、 水 、 palladium diacetate 、 lithium hydroxide 、 三环己基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  SAR analysis of innovative selective small molecule antagonists of sphingosine-1-phosphate 4 (S1P4) receptor

  摘要：

  Recent evidence suggests an innovative application of chemical modulators targeting the S1P(4) receptor as novel mechanism-based drugs for the treatment of influenza virus infection. Modulation of the S1P(4) receptor may also represent an alternative therapeutic approach for clinical conditions where reactive thrombocytosis is an undesired effect or increased megakaryopoiesis is required. With the exception of our recent research program disclosure, we are not aware of any selective S1P(4) antagonists reported in the literature to date. Herein, we describe complementary structure-activity relationships (SAR) of the high-throughput screening (HTS)-derived hit 5-(2,5-dichlorophenyl)-N-(2,6-dimethylphenyl)furan-2-carboxamide and its 2,5-dimethylphenyl analog. Systematic structural modifications of the furan ring showed that both steric and electronic factors in this region have a significant impact on the potency. The furan moiety was successfully replaced with a thiophene or phenyl ring maintaining potency in the low nanomolar range and high selectivity against the other S1P receptor subtypes. By expanding the molecular diversity within the hit-derived class, our SAR study provides innovative small molecule potent and selective S1P(4) antagonists suitable for in vivo pharmacological validation of the target receptor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.132
• 作为产物：
  描述：

  3-呋喃甲酸甲酯 在 溴 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以24%的产率得到Methyl 5-bromofuran-3-carboxylate
  参考文献：
  名称：

  Antimuscarinic 3-(2-Furanyl)quinuclidin-2-ene Derivatives:  Synthesis and Structure−Activity Relationships

  摘要：

  A series of 25 derivatives of the muscarinic antagonist 3-(2-furanyl)quinuclidin-2-ene (4) was synthesized and evaluated for muscarinic and antimuscarinic properties. Substitution at all three positions of the furan ring has been investigated. The affinities of the new compounds were determined by competition experiments in homogenates of cerebral cortex, heart, parotid gland, and urinary bladder from guinea pigs using (-)-[H-3]-3-quinuclidinyl benzilate as the radioligand, and the antimuscarinic potency was determined in a functional assay on isolated guinea pig urinary bladder using carbachol as the agonist. Several of the novel derivatives displayed high muscarinic affinities. Whereas the affinity of lead compound 4 for cortical muscarinic receptors is moderate (K-i 300 nM), it is much higher for the 6-methyl (49; K-i = 12 nM), 5-ethyl (52; K-i = 7.4 nM), 5-bromo (33; K-i = 6.4 nM), and 3-phenyl (49; K-i = 2.8 nM) substituted derivatives. The substituent-induced increases in affinity do not appear to be additive as a 5-bromo-3-phenyl (54), and a 5-methyl-3-phenyl (55) substitution pattern only slightly increases affinity (K-i = 1.55 and 2.39 nM, respectively). The conformational preferences of the 3-phenyl (49) and 5-phenyl (51) derivatives were studied by X-ray crystallography and molecular mechanics calculations. Because of the observed high affinity of 49, a series of 16 meta-and para-substituted analogues of 49 was synthesized and tested. derivative (68) exhibited more than 10-fold improvement in affinity as compared to 49. The structure-activity relationships of the new series are well described with QSAR and CoMFA models.

  DOI：

  10.1021/jm970346t

文献信息

• Novel Heterocyclic Compounds as Pesticides
  申请人：MÜHLTHAU Friedrich August

  公开号：US20120094837A1

  公开（公告）日：2012-04-19

  The present invention relates to novel heterocyclic compounds, to processes for preparation thereof and to the use thereof for controlling animal pests, which include arthropods and especially insects.

  本发明涉及新颖的杂环化合物，其制备过程以及用于控制动物害虫的用途，包括节肢动物，尤其是昆虫。
• NEUE HETEROCYCLISCHE VERBINDUNGEN ALS SCHÄDLINGSBEKÄMPFUNGSMITTEL
  申请人：Bayer Intellectual Property GmbH

  公开号：EP2593447A2

  公开（公告）日：2013-05-22
• 3-PYRIDYL-HETEROARYLCARBOXAMIDVERBINDUNGEN ALS SCHÄDLINGSBEKÄMPFUNGSMITTEL
  申请人：Bayer Intellectual Property GmbH

  公开号：EP2593447B1

  公开（公告）日：2016-08-17
• US9233951B2
  申请人：——

  公开号：US9233951B2

  公开（公告）日：2016-01-12
• [DE] NEUE HETEROCYCLISCHE VERBINDUNGEN ALS SCHÄDLINGSBEKÄMPFUNGSMITTEL<br/>[EN] NEW HETEROCYCLIC COMPOUNDS AS PESTICIDES<br/>[FR] NOUVEAUX COMPOSÉS HÉTÉROCYCLIQUES SERVANT D'AGENTS DE LUTTE CONTRE LES NUISIBLES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2012007500A2

  公开（公告）日：2012-01-19

  Die vorliegende Anmeldung betrifft neue heterocyclische Verbindungen, Verfahren zu Ihrer Herstellung und ihre Verwendung zur Bekämpfung von tierischen Schädlingen, zu denen Arthropoden und insbesondere Insekten zählen.