(6-oxo-4-phenyl-1,6-dihydro-pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester | 50892-50-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (6-oxo-4-phenyl-1,6-dihydro-pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester
• 英文别名: (4-hydroxy-6-phenyl-2-pyrimidinylthio)acetic acid ethyl ester；(4-hydroxy-6-phenyl-pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester；(4-Hydroxy-6-phenyl-2-pyrimidinylthio)acetic acid ethyl ester；ethyl 2-[(6-oxo-4-phenyl-1H-pyrimidin-2-yl)sulfanyl]acetate
• CAS: 50892-50-7
• 化学式: C₁₄H₁₄N₂O₃S
• 分子量: 290.343
• InChiKey: YDXPGTAZHLTZPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6-oxo-4-phenyl-1,6-dihydro-pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester 以 三氯氧磷 为溶剂， 生成 (4-chloro-6-phenyl-pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester
  参考文献：
  名称：

  2-PYRIMIDINYLTHIO)ALKANOIC ACIDS, ESTERS, AMIDES AND HYDRAZIDES

  摘要：

  (2-嘧啶基硫)烷酸，酯，酰胺和肼以及各种4-和6-取代衍生物，如下所示的结构式：##SPC1## 其中R和R.sup.2独立为--H或较低的烷基；R.sup.1为--H，-卤素或较低的烷氧基；Z为--OH，OM，较低的烷氧基或--(NH).sub.1 --NH.sub.2，其中p为0至1，M为碱金属，碱土金属或铵阳离子；Y为芳基，氨基或取代氨基基团；m为0至2的整数，在温血动物中表现出抗脂质活性。

  公开号：

  US03940394A1
• 作为产物：
  描述：

  溴乙酸乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (6-oxo-4-phenyl-1,6-dihydro-pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester
  参考文献：
  名称：

  [EN] NOVEL PYRIMIDINE COMPOUNDS, PROCESS FOR THEIR PREPARATION AND COMPOSITIONS CONTAINING THEM
  [FR] NOUVEAUX COMPOSES DE PYRIMIDINE, LEUR PROCEDE DE PREPARATION, ET COMPOSITIONS LES CONTENANT

  摘要：

  公开号：

  WO2006034473A3

文献信息

• 2-PYRIMIDINYLTHIO)ALKANOIC ACIDS, ESTERS, AMIDES AND HYDRAZIDES
  申请人：——

  公开号：US03940394A1

  公开（公告）日：1976-02-24

  (2-Pyrimidinylthio)alkanoic acid, esters, amides and hydrazides as well as various 4- and 6-substituted derivatives thereof as depicted by the structural formula: ##SPC1## In which R and R.sup.2 are independently --H or lower alkyl; R.sup.1 is --H, -halo or lower alkoxy; Z is --OH, OM, lower alkoxy or --(NH).sub.1 --NH.sub.2, wherein p is 0 to 1 and M is an alkali metal, alkaline earth metal or ammonium cation; Y is an aryl, amino or substituted amino radical; and m is an integer from 0 to 2, exhibit anti-lipemic activity in warm-blooded animals.

  (2-嘧啶基硫)烷酸，酯，酰胺和肼以及各种4-和6-取代衍生物，如下所示的结构式：##SPC1## 其中R和R.sup.2独立为--H或较低的烷基；R.sup.1为--H，-卤素或较低的烷氧基；Z为--OH，OM，较低的烷氧基或--(NH).sub.1 --NH.sub.2，其中p为0至1，M为碱金属，碱土金属或铵阳离子；Y为芳基，氨基或取代氨基基团；m为0至2的整数，在温血动物中表现出抗脂质活性。
• Synthesis of Pyrimidine, Thiazolopyrimidine, Pyrimidotriazine and Triazolopyrimidine Derivatives and their Biological Evaluation
  作者：Fawzy A. Attaby、Sanaa M. Eldin

  DOI：10.1515/znb-1999-0614

  日期：1999.6.1

  Pyrimidin-4-one-2-thione (3) was synthesized via the reaction of thiourea (1) with ethyl benzoylacetate (2) and was taken as a starting material for the present study via its reactions with the halogen-containing reagents 6a-d and lOa-c to give the corresponding thiazolopyrimidines 8, 9 and 12a-c. The 2-hydrazino derivatives 5 were synthesized either via the reaction of 3 or 4 with hydrazine hydrate. Compound 5 reacted with 6a-c and lOa-c to give the corresponding pyrimidotriazines 17a-c and 19 respectively. Also, compound 5 reacted with the active methylene-containing reagents 13 and 2a,b to give the corresponding 2-pyrazolopyrimidines 15 and 22a,b respectively. On the other hand, the triazolopyrimidines 21a,b and 30a,b were also obtained via the reaction of 5 with each of formic acid, acetic anhydride, ethyl chloroformate and carbon disulfide respectively. Some of the newly synthesized heterocyclic derivatives were tested for their biological activity

  通过将硫脲（1）与乙基苯甲酰乙酸酯（2）反应合成了嘧啶-4-酮-2-硫酮（3），并将其作为起始物质与含卤素试剂6a-d和lOa-c反应，得到相应的噻唑嘧啶类化合物8、9和12a-c。2-叠氮衍生物5可以通过3或4与叠氮酸水合物反应合成。化合物5与6a-c和lOa-c反应，得到相应的嘧啶三嗪类化合物17a-c和19。此外，化合物5与含活性亚甲基的试剂13和2a、b反应，分别得到相应的2-吡唑嘧啶类化合物15和22a、b。另外，三唑嘧啶类化合物21a、b和30a、b也是通过5分别与甲酸、乙酸酐、氯甲酸乙酯和二硫化碳反应而获得的。一些新合成的杂环衍生物已经进行了生物活性测试。
• Reaction of 6-Methyl-2-Thiouracil and 6-Phenyl-2-Thiouracil with Chloro-β-Dicarbonyl and Bromo-β-Dicarbonyl Compounds and Their Nitrile Analogs
  作者：A. A. Yavolovskii、Yu. E. Ivanov、M. S. Fonari、L. Croitor、L. V. Grishchuk、R. Yu. Ivanova、G. L. Kamalov

  DOI：10.1002/jhet.2525

  日期：2016.11

  Derivatives of 2‐methylidene‐1,3‐dihydropyrimidin‐4‐ones 2a, 2b, 2c, 2d, 2e, 2f, 2g were synthesized by interaction of 6‐methyl‐2‐thiouracil and 6‐phenyl‐2‐thiouracil 1a, 1b with some activated halogenides: diethyl bromomalonate, ethyl 2‐chloro‐3‐oxobutanoate, ethyl 2‐bromocyanoacetate, 2‐bromo‐5,5‐dimethylcyclohexan‐1,3‐dione, and bromomalononitrile. The boiling of 1a with ethyl 2‐bromocyanoacetate

  的2-亚甲基-1,3-二氢嘧啶-4-酮衍生物2A，2B，2C，2D，2E，2F，2克通过的相互作用合成6-甲基-2-硫尿嘧啶和6-苯基-2-硫尿嘧啶1A，1b与一些活化的卤化物：溴代丙二酸二乙酯，2-氯-3-氧代丁酸乙酯，2-溴氰基乙酸乙酯，2-溴-5,5-二甲基环己基1,3-二酮和溴代丙二腈。的沸点1A具有在的噻唑乙醇和EtONa导致分子内环化及形成混合物2- bromocyanoacetate [3,2-一个]嘧啶-5-酮3。1a与3-氯戊烷-2,4-二酮和2-溴-1,3-二苯丙烷-1,3-二酮相互作用产生相应的S-取代的硫代嘧啶4a，4b。通常，1b S烷基化产物不易硫磺挤出。在EtONa不存在下1b与溴代丙二酸二乙酯的反应在S-烷基化步骤中停止，而在乙醇或PPh 3中在EtONa存在下在二恶烷2-（乙氧基羰基甲基）硫代-6-苯基-1,3-二氢嘧啶-4中反应（1H）-一个6唯一形成。讨论了2-（1
• Structure Based Library Design (SBLD) for new 1,4-dihydropyrimidine scaffold as simultaneous COX-1/COX-2 and 5-LOX inhibitors
  作者：Deepak Lokwani、Rajaram Azad、Aniket Sarkate、Pallu Reddanna、Devanand Shinde

  DOI：10.1016/j.bmc.2015.06.008

  日期：2015.8

  The various scaffolds containing 1,4-dihydropyrimidine ring were designed by considering the environment of the active site of COX-1/COX-2 and 5-LOX enzymes. The structure-based library design approach, including the focused library design (Virtual Combinatorial Library Design) and virtual screening was used to select the 1,4-dihydropyrimidine scaffold for simultaneous inhibition of both enzyme pathways (COX-1/COX-2 and 5-LOX). The virtual library on each 1,4-dihydropyrimidine scaffold was enumerated in two alternative ways. In first way, the chemical reagents at R groups were filtered by docking of scaffold with single position substitution, that is, only at R-1, or R-2, or R-3, ... R-n on COX-2 enzyme using Glide XP docking mode. The structures that do not dock well were removed and the library was enumerated with filtered chemical reagents. In second alternative way, the single position docking stage was bypassed, and the entire library was enumerated using all chemical reagents by docking on the COX-2 enzyme. The entire library of approximately 15,629 compounds obtained from both ways after screening for drug like properties, were further screened for their binding affinity against COX-1 and 5-LOX enzymes using Virtual Screening Workflow. Finally, 142 hits were obtained and divided into two groups based on their binding affinity for COX-1/COX-2 and for both enzyme pathways (COX-1/COX-2 and 5-LOX). The ten molecules were selected, synthesized and evaluated for their COX-1, COX-2 and 5-LOX inhibiting activity. (C) 2015 Elsevier Ltd. All rights reserved.
• US3940394A
  申请人：——

  公开号：US3940394A

  公开（公告）日：1976-02-24