Methyl 6-methyl-2-naphthyl-4-thioxo-2H,3H,5H-3,5-diazinecarboxylate | 314051-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 6-methyl-2-naphthyl-4-thioxo-2H,3H,5H-3,5-diazinecarboxylate
• 英文别名: methyl 6-methyl-4-naphthalen-1-yl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 314051-89-3
• 化学式: C₁₇H₁₆N₂O₂S
• 分子量: 312.392
• InChiKey: RFHLVYJSORYQOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 6-methyl-2-naphthyl-4-thioxo-2H,3H,5H-3,5-diazinecarboxylate 、 3-溴丙炔 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以93%的产率得到methyl 3,7-dimethyl-5-(naphthalen-1-yl)-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  高效5-芳基-5H-噻唑并[3,2-a]嘧啶的简单高效一锅合成

  摘要：

  据报道，在很短的时间内，可以通过4-芳基二氢硫代嘧啶与炔丙基溴的反应，一锅经济，高效地合成多功能5H-噻唑并[3,2-a]嘧啶。

  DOI：

  10.1002/jhet.831
• 作为产物：
  描述：

  1-萘甲醛 、 乙酰乙酸甲酯 、 硫脲 在 organosulfonic acid-functionalized periodic mesoporous organosilicas 作用下， 以 neat (no solvent) 为溶剂， 反应 5.5h， 以91%的产率得到Methyl 6-methyl-2-naphthyl-4-thioxo-2H,3H,5H-3,5-diazinecarboxylate
  参考文献：
  名称：

  通过控制催化剂的疏水/亲水表面平衡来提高三组分Biginelli与Hantzsch反应的选择性

  摘要：

  两种介孔固体酸SBA-15-PrSO 3 H 1，SBA-15-Ph-PrSO 3 H 2和基于周期性介孔有机硅（PMO）的固体酸Et-PMO-Me-PrSO的催化活性和选择性在无溶剂条件下，在醛，β-酮酸酯和尿素或硫脲的环境友好的单锅三组分Biginelli反应中比较了具有不同理化表面性质的3 H 3。在这些介孔固体酸催化剂中，3，在活性位点所在的纳米空间（介孔通道）中具有疏水/疏水平衡，在Biginelli反应中被发现是选择性更高的催化系统。它可以产生相应的3,4-二氢嘧啶-2-酮\硫酮（DHPM）5衍生物，产率高，选择性好。值得注意的是，在存在1的条件下进行苯甲醛，乙酸乙酰甲酯和尿素的三组分偶联反应时，会生成Hantzsch二氢吡啶4（≈37％）和Biginelli dihydropyrimidinone 5（≈49％）的混合物，而与2相同的反应（催化剂负载量也为1 mol％）提供了

  DOI：

  10.1002/cctc.201300739

文献信息

• Synthesis, characterization and biological evaluation of thiazolopyrimidine derivatives
  作者：H NAGARAJAIAH、I M KHAZI、NOOR SHAHINA BEGUM

  DOI：10.1007/s12039-012-0271-z

  日期：2012.7

  activity was evaluated against four bacterial strains and one fungal species. Few of the derivatives exhibited antibacterial and antifungal activities. We have reported the synthesis of some thiazolopyrimidine derivatives by cyclo-condensation of dihydropyrimidine with halo esters. Crystal structure analysis of one of the derivatives has been carried out. Some of the derivatives exhibited antibacterial

  通过在回流条件下用乙醇处理α-卤代酯与3，4-二氢嘧啶2-硫酮，可制备不同的噻唑并嘧啶取代的二酯，收率71-85％。IR，1 HNMR，13 CNMR和元素分析用于表征这些化合物。用单晶X验证了一种产物5-苯基-3,7-二甲基-5H-噻唑并[3,2-a]嘧啶-2,6-二羧酸二乙酯（3e）的晶体和分子结构。射线衍射法。评价了对四种细菌菌株和一种真菌物种的抗菌活性。很少有衍生物表现出抗菌和抗真菌活性。 我们已经报道了通过二氢嘧啶与卤代酯的环缩合反应合成一些噻唑并嘧啶衍生物。已经对一种衍生物进行了晶体结构分析。一些衍生物表现出抗菌和抗真菌活性。
• Hydrophobicity-enhanced magnetic solid sulfonic acid: A simple approach to improve the mass transfer of reaction partners on the surface of the heterogeneous catalyst in water-generating reactions
  作者：Akbar Mobaraki、Barahman Movassagh、Babak Karimi

  DOI：10.1016/j.apcata.2013.12.018

  日期：2014.2
• Copper(I) complexes of methyl 4-aryl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione-5-carboxylates. Synthesis, characterization and activity in human breast cancer cells
  作者：N. González-Ballesteros、D. Pérez-Álvarez、M.S.C. Henriques、B.F.O. Nascimento、M. Laranjo、K. Santos、J. Casalta-Lopes、A.M. Abrantes、M.F. Botelho、M. Pineiro、J.A. Paixão、M.C. Rodríguez-Argüelles

  DOI：10.1016/j.ica.2015.09.012

  日期：2015.11

  New copper(I) complexes of four methyl 4-aryl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione-5-carboxylate ligands, where the aryl group is phenyl (HL1), 1-naphthalenyl (HL2), 2-bromophenyl (HL3) and 2-chlorophenyl (HL4), have been synthesized. Structural characterization was carried out using different techniques, such as elemental analysis, mass spectrometry, molar conductivity, magnetic susceptibility, FTIR, UV-Vis/luminescence and NMR spectroscopies, and allowed us to propose the general formula [CuCl(HL)(2)] for all complexes. Furthermore, X-ray studies of ligands HL2 and HL3 and the complex [CuCl(HL2)(2)]center dot 3dmso have been performed. The complex crystallizes in the triclinic space group P (1) over bar and adopts a less common, almost perfect, trigonal planar coordination geometry, through the two sulfur atoms of the ligands and one chlorine atom bonded to the metal. The intramolecular hydrogen bonds between the chlorine and the N1H stabilize the structure of the complex. Evaluation of the in vitro activity against human breast cancer representatives of hormonal receptor positive (MCF7) and triple negative (HCC1806) tumors revealed a higher activity in the complexes than in the ligands. Considering particularly HCC1806 cells for which no targeted treatment is available, complexes [CuCl (HL1)(2)] and [CuCl(HL3)(2)] exhibited IC50 values of 5.51 and 5.30 mu M, respectively, which are lower than the currently used chemotherapeutic drugs. (C) 2015 Elsevier B.V. All rights reserved.
• [EN] 2-THIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE DERIVATIVES<br/>[FR] DERIVES DE 2-THIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE
  申请人：ONO PHARMACEUTICAL CO

  公开号：WO2002066443A2

  公开（公告）日：2002-08-29

  The present invention is related to: (1) neutral sphingomyelinase inhibitors containing 2-thioxo 1,2,3,4-tetrahydropyrimidine derivatives of the formula (I): wherein all of the symbols have the same meanings as described hereinbefore, or a non-toxic salt thereof, a hydrate thereof, or a prodrug thereof as active ingredient, (2) novel 2-thioxo-1,2,3,4-tetrahydropyrimidine derivatives of the formula (I): wherein all of the symbols have the same meanings as described hereinbefore, or a non-toxic salt thereof, a hydrate thereof, or a prodrug thereof, (3) some novel specific compounds, and (4) process for the preparation of the compounds of the formula (Ia), or a prodrug thereof. The compounds of the present invention of the formulae (I) and (Ia) are neutral sphingomyelinase inhibitors and therefore are useful for the treatment and/or prevention of arteriosclerosis, cerebral ischemia, cardiac ischemia, lung injury, renal injury, GVHD (graft versus host diseases), transplant rejection, HIV, etc.
• A Simple and Efficient One-Pot Synthesis of Multifunctional 5-Aryl-<i>5H</i>-thiazolo[3,2-a]pyrimidines
  作者：Seerat Fatima、Anindra Sharma、Rahul Sharma、Rama P. Tripathi

  DOI：10.1002/jhet.831

  日期：2012.5

  One‐pot economical and efficient synthesis of multifunctional 5H‐thiazolo[3,2‐a]pyrimidines by the reaction of 4‐aryl dihydrothiopyrimidines with propargyl bromide in the presence of inorganic base has been reported in very short time.

  据报道，在很短的时间内，可以通过4-芳基二氢硫代嘧啶与炔丙基溴的反应，一锅经济，高效地合成多功能5H-噻唑并[3,2-a]嘧啶。