dimethylthiocarbamic acid S-(4-acetyl-2-methoxy-phenyl) ester | 69114-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethylthiocarbamic acid S-(4-acetyl-2-methoxy-phenyl) ester
• 英文别名: 4-dimethylcarbamoylsulfanyl-3-methoxyacetophenone；S-(4-acetyl-2-methoxyphenyl) N,N-dimethylcarbamothioate
• CAS: 69114-72-3
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: PJEKJXYRJUHAON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethylthiocarbamic acid S-(4-acetyl-2-methoxy-phenyl) ester 在 氢氧化钾 作用下， 以 水 、 乙二醇 为溶剂， 生成 1-(4-thio-3-methoxyphenyl)ethanone
  参考文献：
  名称：

  Aryl-substituted acrylamides with Leukotriene B4 (LTB-4) receptor antagonist activity

  摘要：

  本发明涉及一种式子（I）的化合物，其中W为CH或N；R为（单环或双环芳基或杂环芳基）-较低烷基；R1为氢或较低烷基；R2和R3为氢、较低烷基、较低烷氧基-较低烷基或芳基-较低烷基；或者R2和R3结合在一起，用较低烷基烷基可选地中断的O、NH、N-较低烷基或S表示，以形成与酰胺氮原子形成环的环；X为O、S、SO、S2或直接键；X1为O、S、SO、SO2或直接键；Y为直接键、较低烷基或较低烷基亚甲基；Z为羧基、5-四唑基、羟甲基或以药学上可接受的酯形式衍生的羧基，并且其药学上可接受的盐；它们有用作LTB-4拮抗剂。

  公开号：

  US06291530B1
• 作为产物：
  描述：

  香草乙酮 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 dimethylthiocarbamic acid S-(4-acetyl-2-methoxy-phenyl) ester
  参考文献：
  名称：

  Carboxy-Substituted Cinnamides:  A Novel Series of Potent, Orally Active LTB₄ Receptor Antagonists

  摘要：

  A series of carboxy-substituted cinnamides were investigated as antagonists of the human cell surface leukotriene B-4 (LTB4) receptor. Binding was determined through measurement of [H-3]-LTB4 displacement from human neutrophils. Receptor antagonism was confirmed through a functional assay, which measures inhibition of Ca2+ release in human neutrophils. Potent antagonists were discovered through optimization of a random screening hit, a p-(alpha-methylbenzyloxy)cinnamide, having low-micromolar activity. Substantial improvement of in vitro potency was realized by the attachment of a carboxylic acid moiety to the cinnamide phenyl ring through a flexible tether, leading to identification of compounds with low-nanomolar potency. Modification of the benzyloxy substituent, either through ortho-substitution on the benzyloxy phenyl group or through replacement of the ether oxygen with a methylene or sulfur atom, produced achiral antagonists of equal or greater potency. The most potent compounds in vitro were assayed for oral activity using the arachidonic acid-induced mouse ear edema model of inflammation. Several compounds in this series were found to significantly inhibit edema formation and myeloperoxidase activity in this model up to 17 h after oral administration. Representatives of this series have been shown to be potent and long-acting orally active inhibitors of the LTB4 receptor.

  DOI：

  10.1021/jm980540v

文献信息

• Isoxazole derivatives as peroxisome proliferator-activated receptors agonists
  申请人：Fukui Yoshikazu

  公开号：US20070054902A1

  公开（公告）日：2007-03-08

  A compound of formula (I): (wherein R 1 -R 10 are each independently hydrogen, halogen, optionally substituted lower alkyl or the like, X 1 is —O—, —S—, —NR 11 — (wherein R 11 is hydrogen, lower alkyl or the like), —CR 12 R 13 CO—, —(CR 12 R 13 )mO—, —O(CR 12 R 13 )m- (wherein R 12 and R 13 are each independently hydrogen or lower alkyl and m is a integer between 1 and 3) or the like, X 2 is a bond, —O—, —S—, —NR 14 — (wherein R 14 is hydrogen, lower alkyl or the like, R 14 and R 6 can be taken together with the neighboring atom to form a ring) or —CR 15 R 16 — (wherein R 15 and R 16 are each independently hydrogen or lower alkyl, R 15 and R 6 or R 10 can be taken together with the neighboring carbon atom to form a ring, R 16 and R 9 can be joined together to form a bond), X 3 is COOR 17 , C(═NR 17 )NR 18 OR 19 or the like), a pharmaceutically acceptable salt or a solvate thereof.

  化合物的化学式为（I）：（其中R1-R10各自独立地为氢，卤素，可选择性取代的低碳基或类似物，X1为—O—，—S—，—NR11—（其中R11为氢，低碳基或类似物），—CR12R13CO—，—（CR12R13）mO—，—O（CR12R13）m-（其中R12和R13各自独立地为氢或低碳基，m为1到3之间的整数）或类似物，X2为键，—O—，—S—，—NR14—（其中R14为氢，低碳基或类似物，R14和R6可以与相邻的原子结合形成环）或—CR15R16—（其中R15和R16各自独立地为氢或低碳基，R15和R6或R10可以与相邻的碳原子结合形成环，R16和R9可以结合在一起形成键），X3为COOR17，C（═NR17）NR18OR19或类似物），其药学上可接受的盐或溶剂化物。
• ISOXAZOLE DERIVATIVE HAVING AGONISTIC ACTIVITY AGAINST PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR
  申请人：SHIONOGI & CO., LTD.

  公开号：EP1690538A1

  公开（公告）日：2006-08-16

  A compound of formula (I) : (wherein R1-R10 are each independently hydrogen, halogen, optionally substituted lower alkyl or the like, X1 is -O-, -S-, -NR11- (wherein R11 is hydrogen, lower alkyl or the like), -CR12R13CO-, -(CR12R13)mO-, -O(CR12R13)m- (wherein R12 and R13 are each independently hydrogen or lower alkyl and m is a integer between 1 and 3) or the like, X2 is a bond, -O-, -S-, -NR14- (wherein R14 is hydrogen, lower alkyl or the like, R14 and R6 can be taken together with the neighboring atom to form a ring) or -CR15R16-(wherein R15 and R16 are each independently hydrogen or lower alkyl, R15 and R6 or R10 can be taken together with the neighboring carbon atom to form a ring, R16 and R9 can be joined together to form a bond), X3 is COOR17, C( = NR17)NR18OR19 or the like), a pharmaceutically acceptable salt or a solvate thereof.

  式 (I) 的化合物： 其中 R1-R10各自独立地为氢、卤素、任选取代的低级烷基或类似物，X1为-O-、-S-、-NR11-（其中R11为氢、低级烷基或类似物）、-CR12R13CO-、-(CR12R13)mO-、-O(CR12R13)m-（其中R12和R13各自独立地为氢或低级烷基，m为1至3之间的整数）或类似物、 X2 是键、-O-、-S-、-NR14-（其中 R14 是氢、低级烷基或类似物，R14 和 R6 可与邻近原子一起形成环）或-CR15R16-（其中 R15 和 R16 各自独立地是氢或低级烷基、R15和R6或R10可与邻近的碳原子结合形成环，R16和R9可结合形成键），X3为COOR17、C( = NR17)NR18OR19或类似物），其药学上可接受的盐或溶液。
• EP1690538
  申请人：——

  公开号：——

  公开（公告）日：——
• Structural Factors Affecting Cytotoxic Activity of (<i>E</i>)-1-(Benzo[<i>d </i>][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one Derivatives
  作者：Marek T. Konieczny、Anita Bułakowska、Justyna Polak、Danuta Pirska、Wojciech Konieczny、Patrycja Gryń、Andrzej Skladanowski、Michał Sabisz、Krzysztof Lemke、Anna Pieczykolan、Marlena Gałązka、Katarzyna Wiciejowska、Joanna Wietrzyk

  DOI：10.1111/cbdd.12296

  日期：2014.7

  Derivatives of (E)‐1‐(5‐alkoxybenzo[d][1,3]oxathiol‐6‐yl)‐3‐phenylprop‐2‐en‐1‐one demonstrated exceptionally high in vitro cytotoxic activity, with IC50 values of the most active derivatives in the nanomolar range. To identify structural fragments necessary for the activity, several analogs deprived of selected fragments were prepared, and their cytotoxic activity was tested. It was found that the activity depends on combined effects of (i) the heterocyclic ring, (ii) the alkoxy group at position 5 of the benzoxathiole ring, and (iii) the substituents in the phenyl ring B. Replacement of the sulfur atom by oxygen does not influence the activity. None of the listed structural fragments alone assured high cytotoxic activity.
• ARYL-SUBSTITUTED ACRYLAMIDES WITH LEUKOTRIENE B4 (LTB-4) RECEPTOR ANTAGONIST ACTIVITY
  申请人：Novartis AG

  公开号：EP0942903A1

  公开（公告）日：1999-09-22