6-[3-(2-hydroxy-1-methylethylcarbamoyl)phenyl]hex-5-ynoic acid | 863713-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-[3-(2-hydroxy-1-methylethylcarbamoyl)phenyl]hex-5-ynoic acid
• 英文别名: 6-[3-(2-Hydroxy-1-methyl-ethylcarbamoyl)phenyl]-hex-5-ynoic acid；6-[3-(1-hydroxypropan-2-ylcarbamoyl)phenyl]hex-5-ynoic acid
• CAS: 863713-63-7
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: YOSIYUAGQVMRKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-[3-(2-hydroxy-1-methylethylcarbamoyl)phenyl]hex-5-ynoic acid 以53的产率得到3-(5-dimethylcarbamoylpent-1-ynyl)-N-(2-hydroxy-1-methylethyl)benzamide
  参考文献：
  名称：

  Modulator

  摘要：

  本公开涉及式（I）的化合物或其药学上可接受的盐，其中Z从OH，NHCH2CH2F，NHCH（Me）CH2OH和NHCH2CH2OH中选取；X是烷基，烯基或炔基，每个基团可以选择性地被一个或多个取代基所取代，所述取代基从烷基，COOH，CO2-烷基，烯基，CN，NH2，羟基，卤素，烷氧基，CF3和硝基中选择；Y是极性官能团，从OH，NO2，CN，COR3，COOR3，NR3R4，CONR3R4，SO3H，SO2—R3，SO2NR3R4和CF3中选择，其中R3和R4各自独立地是氢或烃基团；A是苯基或吡啶基；B是（CH2）n，其中n为0；但要求：当A是苯基，且Z为OH时，X-Y不是C≡C-（CH2）2CO2H，C≡C-（CH2）2CO2Me，（CH2）4CO2H。提供了这种化合物作为治疗肌肉疾病，胃肠疾病，或控制痉挛或震颤的药物的用途。

  公开号：

  US09120723B2
• 作为产物：
  描述：

  5-己炔酸 、 N-(2-hydroxy-1-methylethyl)-3-iodobenzamide 以giving product (4)(1.87 g, 6.42 mmol; 99% yield)的产率得到6-[3-(2-hydroxy-1-methylethylcarbamoyl)phenyl]hex-5-ynoic acid
  参考文献：
  名称：

  MODULATOR

  摘要：

  本发明涉及化合物(I)的配方，或其药学上可接受的盐。

  公开号：

  US20130123356A1

文献信息

• [EN] COMPOUNDS FOR TREATING DISORDERS ASSOCIATED WITH BK CHANNEL MODULATION<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DE TROUBLES ASSOCIÉS À LA MODULATION DU CANAL BK
  申请人：CANBEX THERAPEUTICS LTD

  公开号：WO2016128771A1

  公开（公告）日：2016-08-18

  The present invention relates to a compound of formula I, or a pharmaceutically acceptable salt, solvate or prodrug thereof, wherein: Z is OR16 or NR17R18; R16 is H or alkyl; R17 is H or alkyl; R18 is alkyl or cycloalkyl, each of which is optionally substituted by one or more substituents selected from OH, halogen and COOR11; X is a group selected from -C≡C-

  本发明涉及一种式I的化合物，或其药学上可接受的盐、溶剂或前药，其中：Z为OR16或NR17R18；R16为H或烷基；R17为H或烷基；R18为烷基或环烷基，每个烷基或环烷基可选择地被一个或多个OH、卤素和COOR11取代；X为从-C≡C-<(CH2)P-；-C噻唑啉中选择的杂环基；其中R2、R3和R4中的每一个独立地为H或烷基；或R3和R4与它们连接的氮一起形成一个5或6-成员的杂环烷基或杂环烯基基团，所述的杂环烷基或杂环烯基基团可选择地含有一个或多个进一步从O、N、CO和S中选择的基团，其中R9、R10、R11、R12、R13、R14和R15中的每一个独立地为H或烷基；用于治疗与BK通道调节相关的疾病。
• [EN] PROCESS FOR PREPARING CARBOXYLIC ACID AMIDES USEFUL IN THE TREATMENT OF MUSCULAR DISORDERS<br/>[FR] PROCÉDÉ
  申请人：UCL BUSINESS PLC

  公开号：WO2010116116A1

  公开（公告）日：2010-10-14

  The present invention relates to a process for preparing a compound of formula wherein: R2 is cycloalkyl or alkyl, each of which may be optionally substituted; Y is -CONR3R4, -CN or CO2R5; R3, R4 and R5 are each independently H or alkyl; n is 1 to 6; wherein said process comprising the steps of : (i) treating a compound of formula (IV), where R1 is alkyl, with a compound of formula (V) and forming a compound of formula (IIIb); (ii) treating said compound of formula (IIIb) with a compound of formula (Il) to form a compound of formula (I).

  本发明涉及一种制备化合物的过程，其化学式为其中：R2为环烷基或烷基，每种均可选择性地被取代；Y为-CONR3R4，-CN或CO2R5；R3、R4和R5分别独立地为H或烷基；n为1至6；其中所述过程包括以下步骤：(i) 用具有化学式（IV）的化合物处理化学式（V）的化合物，并形成化学式（IIIb）的化合物；(ii) 用化学式（IIIb）的化合物处理化学式（Il）的化合物，形成化学式（I）的化合物。
• PROCESS FOR PREPARING CARBOXYLIC ACID AMIDES USEFUL IN THE TREATMENT OF MUSCULAR DISORDERS
  申请人：Selwood David

  公开号：US20120101301A1

  公开（公告）日：2012-04-26

  The present invention relates to a process for preparing a compound of formula wherein: R 2 is cycloalkyl or alkyl, each of which may be optionally substituted; Y is —CONR 3 R 4 , —CN or CO 2 R 5 ; R 3 , R 4 and R 5 are each independently H or alkyl; n is 1 to 6; wherein said process comprising the steps of: (i) treating a compound of formula (IV), where R 1 is alkyl, with a compound of formula (V) and forming a compound of formula (IIIb); (ii) treating said compound of formula (IIIb) with a compound of formula (I1) to form a compound of formula (I).

  本发明涉及一种制备以下式子化合物的方法：其中：R2是环烷基或烷基，每个基团都可以选择性地被取代；Y是—CONR3R4，—CN或CO2R5；R3、R4和R5分别是H或烷基；n为1到6；其中所述方法包括以下步骤：(i)用式子(IV)化合物（其中R1是烷基）处理式子(V)化合物，形成式子(IIIb)化合物；(ii)用式子(I1)化合物处理所述式子(IIIb)化合物，形成式子(I)化合物。
• Vascular pharmacology of a novel cannabinoid-like compound, 3-(5-dimethylcarbamoyl-pent-1-enyl)-<i>N</i> -(2-hydroxy-1-methyl-ethyl)benzamide (VSN16) in the rat
  作者：P M Hoi、C Visintin、M Okuyama、S M Gardiner、S S Kaup、T Bennett、D Baker、D L Selwood、C R Hiley

  DOI：10.1038/sj.bjp.0707470

  日期：2007.11

  Background and purpose:A putative novel cannabinoid receptor mediates vasorelaxation to anandamide and abnormal‐cannabidiol and is blocked by O‐1918 and by high concentrations of rimonabant. This study investigates VSN16, a novel water‐soluble agonist, as a vasorelaxant potentially acting at non‐CB1, non‐CB2 cannabinoid receptors in the vasculature.Experimental approach:VSN16 and some analogues were synthesized and assayed for vasodilator activity in the rat third generation mesenteric artery using wire myography. Also carried out with VSN16 were haemodynamic studies in conscious rats and binding studies to CB1 receptors of rat cerebellum.Key results:VSN16 relaxed mesenteric arteries in an endothelium‐dependent manner. The vasorelaxation was antagonized by high concentrations of the classical cannabinoid antagonists, rimonabant and AM 251, as well as by O‐1918, an antagonist at the abnormal‐cannabidiol receptor but not at CB1 or CB2 receptors. It did not affect [3H]CP55,940 binding to CB1 receptors in rat cerebellum. The vasorelaxation was not pertussis toxin‐sensitive but was reduced by inhibition of nitric oxide synthesis, Ca2+‐sensitive K+ channels (KCa) and TRPV1 receptors. In conscious rats VSN16 transiently increased blood pressure and caused a longer‐lasting increase in mesenteric vascular conductance. Structure‐activity studies on vasorelaxation showed a stringent interaction with the target receptor.Conclusions and implications:VSN16 is an agonist at a novel cannabinoid receptor of the vasculature. It acts on the endothelium to release nitric oxide and activate KCa and TRPV1. As it is water‐soluble it might be useful in bringing about peripheral cannabinoid‐like effects without accompanying central or severe cardiovascular responses.British Journal of Pharmacology (2007) 152, 751–764; doi:10.1038/sj.bjp.0707470; published online 24 September 2007
• [EN] MODULATORS OF CANNABINOID RECEPTORS<br/>[FR] MODULATEUR
  申请人：UNIV LONDON

  公开号：WO2005080316A3

  公开（公告）日：2005-11-03