(R)-1-(5-methylfuran-2-yl)propan-1-amine | 473732-94-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-1-(5-methylfuran-2-yl)propan-1-amine
• 英文别名: (1R)-1-(5-methyl-2-furyl)propan-1-amine；(R)-1-(5-methylfuran-2-yl)1-propylamine；(R)-1-(5-methyl-furan-2-yl)-propylamine；(R)-1-(5-methyl-furan-2-yl)propylamine；(R)-1-(5-methylfuran-2-yl)propylamine；(1R)-1-(5-methylfuran-2-yl)propan-1-amine
• CAS: 473732-94-4
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: YLNWJSHBHAFMAT-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险类别：
  8
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险品运输编号：
  3259
• 危险性描述：
  H314
• 包装等级：
  III
• 储存条件：
  存储条件：2-8℃，避光保存。

反应信息

• 作为反应物：
  描述：

  (R)-1-(5-methylfuran-2-yl)propan-1-amine 在 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Discovery of a Selective TRPM8 Antagonist with Clinical Efficacy in Cold-Related Pain

  摘要：

  The transient receptor potential (TRP) family of ion channels comprises nonselective cation channels that respond to a wide range of chemical and thermal stimuli. TRPM8, a member of the melastatin subfamily, is activated by cold temperatures (<28 degrees C), and antagonists of this channel have the potential to treat cold induced allodynia and hyperalgesia. However, TRPM8 has also been implicated in mammalian thermoregulation and antagonists have the potential to induce hypothermia in patients. We report herein the identification and optimization of a series of TRPM8 antagonists that ultimately led to the discovery of PF-05105679. The clinical finding with this compound will be discussed, including both efficacy and its ability to affect thermoregulation processes in humans.

  DOI：

  10.1021/ml500479v
• 作为产物：
  描述：

  在 高碘酸 、 甲胺 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 (R)-1-(5-methylfuran-2-yl)propan-1-amine
  参考文献：
  名称：

  Discovery of 2-Hydroxy-N,N-dimethyl-3-{2-[[(R)-1-(5- methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobut-1-enylamino}benzamide (SCH 527123):  A Potent, Orally Bioavailable CXCR2/CXCR1 Receptor Antagonist

  摘要：

  Structure-activity studies on lead cyclobutenedione 3 led to the discovery of 4 (SCH 527123), a potent, orally bioavailable CXCR2/CXCR1 receptor antagonist with excellent cell-based activity. Compound 4 displayed good oral bioavailability in rat and may be a potential therapeutic agent for the treatment of various inflammatory diseases.

  DOI：

  10.1021/jm0609622

文献信息

• 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
  申请人：Schering Corporation

  公开号：US20040106794A1

  公开（公告）日：2004-06-03

  There are disclosed compounds of the formula 1 or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

  这里公开了用于治疗诸如急性和慢性炎症性疾病以及癌症的趋化因子介导疾病的公式1化合物或其药用可接受的盐或溶剂。
• Synthesis of 2-hydroxy-N,N-dimethyl-3-[[2-[1(R)-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-l]aminobenzamide
  申请人：Schering Corporation

  公开号：US20040209946A1

  公开（公告）日：2004-10-21

  Disclosed is a process for making the compound of formula I: 1 using the compounds of formulas II, Q, and XI or XII: 2 wherein A is selected from the group consisting of Br, Cl and I (with Br being preferred); and R represents (C 1 -C 10 )alkyl. Also disclosed are intermediate compounds that are made in the disclosed process.

  揭示了制备化合物I的过程： 使用化合物II、Q和XI或XII的公式： 其中A选自Br、Cl和I的组，其中Br为首选；R代表(C1-C10)烷基。还揭示了在所述过程中制备的中间化合物。
• [EN] 3, 4-DI-SUBSTITUTED CYCLOBUTENE- 1, 2 -DIONES AS CXCR2 RECEPTOR ANTAGONISTS<br/>[FR] CYCLOBUTÈNE-1,2-DIONES 3,4-DISUBSTITUÉES EN TANT QU'ANTAGONISTES DE RÉCEPTEUR CXCR2
  申请人：NOVARTIS AG

  公开号：WO2010063802A1

  公开（公告）日：2010-06-10

  The present invention relates to compounds of formula (I) wherein R1, R2, Ar, p, R4 and R5 are as defined herein, which are useful for creating diseases which respond to CXCR2 receptor mediators. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

  本发明涉及式（I）中R1、R2、Ar、p、R4和R5如本文所定义的化合物，这些化合物对于产生对CXCR2受体介质有响应的疾病是有用的。还描述了含有这些化合物的药物组合物以及制备这些化合物的方法。
• [EN] PROCESS FOR CONTROLLED CRYSTAL SIZE IN 1,2-SUBSTITUTED 3,4-DIOXO-1-CYCLOBUTENE COMPOUNDS<br/>[FR] PROCÉDÉ POUR OBTENIR UNE TAILLE DE CRISTAUX CONTRÔLÉE DANS DES COMPOSÉS 3,4-DIOXO-1-CYCLOBUTÈNE 1,2-SUBSTITUÉS
  申请人：SCHERING CORP

  公开号：WO2009005802A1

  公开（公告）日：2009-01-08

  This application discloses a novel process for the preparation of 2-Hydroxy-N,N-dimethyl-3-[[2-[[1(R)-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl]amino]benzamide, which has utility, for example, in the treatment of CXC chemokine-mediated diseases.

  该应用程序披露了一种新颖的制备2-羟基-N，N-二甲基-3-[[2-[[1(R)-(5-甲基-2-呋喃基)丙基]氨基]-3,4-二氧杂环丁-1-基]氨基]苯甲酰胺的方法，该方法在治疗CXC趋化因子介导的疾病中具有实用性。
• [EN] PROCESS AND INTERMEDIATES FOR THE SYNTHESIS OF 1,2-SUBSTITUTED 3,4-DIOXO-1-CYCLOBUTENE COMPOUNDS<br/>[FR] PROCÉDÉ ET INTERMÉDIAIRES DE SYNTHÈSE DE COMPOSÉS DE 3,4-DIOXO-1-CYCLOBUTÈNE 1,2-SUBSTITUÉS
  申请人：SCHERING CORP

  公开号：WO2009005801A1

  公开（公告）日：2009-01-08

  This application discloses a novel process for the preparation of 1.2 - substituted 3, 4 - dioxo - 1 - cyclobutene compounds of formula (A), which have utility, for example, in the treatment of CXC chemokine -mediated diseases, and intermediates useful in the synthesis thereof.

  该应用程序披露了一种新颖的制备1,2-取代3,4-二氧基-1-环丁烯化合物（A）的过程，该化合物在治疗CXC趋化因子介导的疾病等方面具有用途，并且还披露了在其合成中有用的中间体。