3-amino-2-thioxo-2,3,5,6,7,8-hexahydro[l]benzothieno[2,3-d]pyrimidin-4(1H)-one | 151094-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 3-amino-2-thioxo-2,3,5,6,7,8-hexahydro[l]benzothieno[2,3-d]pyrimidin-4(1H)-one
• 英文别名: 2,3,5,6,7,8-hexahydro-3-amino-2-thioxo<1>benzothieno<2,3-d>pyrimidin-4(1H)-one；3-amino-2-thioxo-2,3,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-4(1H)-one；3-amino-2-sulfanylidene-5,6,7,8-tetrahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
• CAS: 151094-90-5
• 化学式: C₁₀H₁₁N₃OS₂
• 分子量: 253.349
• InChiKey: PKTOLJZCUIVPGI-UHFFFAOYSA-N

物化性质

• 溶解度：
  26.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-2-thioxo-2,3,5,6,7,8-hexahydro[l]benzothieno[2,3-d]pyrimidin-4(1H)-one 在 sodium hydroxide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1-(4-Methoxy-phenyl)-3-(2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-benzo[4,5]thieno[2,3-d]pyrimidin-3-yl)-thiourea
  参考文献：
  名称：

  新型2-甲硫基-3-取代的5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-4（3H）-的合成，镇痛，抗炎，促溃疡指数和抗菌活性那些。

  摘要：

  通过使（2-甲硫基- 4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3-基）二硫代氨基甲酸甲酯（5）与多种胺。起始原料二硫代氨基甲酸酯（5）是由2-氨基-3-甲乙氧基-4,5,6,7-四氢苯并（b）噻吩（1）合成的。研究了标题化合物的镇痛，抗炎，致溃疡指数和抗菌活性。尽管受试化合物显示出显着的活性，但化合物1-甲基-3-（2-甲硫基-4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3 -基）硫脲（A1），1-二甲基-3-（2-甲硫基-4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3-基）硫脲（A2），

  DOI：

  10.1016/j.ejmech.2006.06.005
• 作为产物：
  描述：

  2-Ethoxythiocarbonylamino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以65%的产率得到3-amino-2-thioxo-2,3,5,6,7,8-hexahydro[l]benzothieno[2,3-d]pyrimidin-4(1H)-one
  参考文献：
  名称：

  Ghorab, M. M.; Heiba, H. I.; El-Gawish, Mona A., Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 106, # 1-4, p. 85 - 90

  摘要：

  DOI：

文献信息

• Reactions with Hydrazonoyl Halides 60¹: Synthesis of Thieno[2′,3′:4,5] Pyrimidino[1,2-<i>b</i>][1,2,4,5]tetrazines, [1]benzothieno[2′,3′:4,5]pyrimidino [1,2-<i>b</i>][1,2,4,5]tetrazines, Pyrazolo[3′,4′:4,5]pyrimidino[1,2-<i>b</i>] [1,2,4,5]tetrazines and Pyrazolo[3,4-<i>d</i>]pyridazines
  作者：Abdou O. Abdelhamid、Zeineb H. Ismail、Anhar Abdel-Aziem

  DOI：10.3184/030823407x256118

  日期：2007.10

  [1]benzothieno-[2′,3′:4,5]pyrimidino[1,2-b][1,2,4,5]tetrazine, pyrazolo [3′,4′:4,5]pyrimidino[1,2-b][1,2,4,5]tetrazine, triazolo[4,3-a]pyrimidin-5(1H)-one, 1-[2-(1-benzofuran-2-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-4-substituted-1,3-thiazol-5-yl}-2-phenyldiazene, 3-acyl-4-(1-benzofuran-2-ylcarbonyl) pyrazole and pyrazolo[3,4-d]pyridazine derivatives could be obtained via reactions of hydrazonoyl halides

  噻吩并[2',3':4,5]嘧啶并[1,2-b][1,2,4,5]四嗪，[1]苯并噻吩-[2',3':4,5]嘧啶[1] ,2-b][1,2,4,5]四嗪，吡唑并 [3',4':4,5]嘧啶并[1,2-b][1,2,4,5]四嗪，三唑并[4] ,3-a]嘧啶-5(1H)-one, 1-[2-(1-benzofuran-2-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-4 -取代-1,3-噻唑-5-基}-2-苯基二氮烯、3-酰基-4-(1-苯并呋喃-2-基羰基)吡唑和吡唑并[3,4-d]哒嗪衍生物可通过反应获得腙酰卤与适当的嘧啶-2-硫酮、3-氨基-5,6-二甲基-2-硫烷基噻吩并[2,3-d]嘧啶-4(3H)-酮、5-氨基-6-巯基-1 -苯基-1,5-二氢吡唑并[3,4-d]嘧啶-4-酮和1-(苯并呋喃-2-基)-3-(二甲氨基)丙-2-烯-1-酮
• Synthesis of some new bioactive 3-amino-2-mercapto-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one derivatives
  作者：B.V. Ashalatha、B. Narayana、K.K. Vijaya Raj、N. Suchetha Kumari

  DOI：10.1016/j.ejmech.2006.11.007

  日期：2007.5

  Nine new 2-(substituted phenyl)/alkyl[1,3,4]thiadiazolo[2,3-b]-6,7,8,9-tetrahydrobenzo(b)thieno[3,2-e]pyr imidin-5(4H)-ones, six new 3-amino-2-[(2-oxo-2-(aryl)ethyl)thio]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyri midin-4(3H)-ones, one 2-mercapto[1,3,4]thiadiazolo[2,3-b]-6,7,8,9-tetrahydrobenzo(b)thieno[3,2-e]pyrimi din-5(4H)-one and one 2-chloromethyl[1,3,4]thiadiazolo[2,3-b]-6,7,8,9-tetrahydrobenzo(b)thieno[3

  九个新的2-（取代苯基）/烷基[1,3,4]噻二唑[2,3-b] -6,7,8,9-四氢苯并（b）噻吩并[3,2-e] pyr imidin-5 （4H）-一个，六个新的3-氨基-2-[（2-氧代-2-（芳基）乙基）硫基] -5,6,7,8-四氢[1]苯并噻吩并[2,3-d] pyri midin-4（3H）-ones，一个2-巯基[1,3,4]噻二唑[2,3-b] -6,7,8,9-四氢苯并（b）thieno [3,2-e]嘧啶din-5（4H）-1和一个2-氯甲基[1,3,4]噻二唑[2,3-b] -6,7,8,9-四氢苯并（b）thieno [3,2-e] py rimidin-5（4H）-one是由3-amino-2-mercapto-5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidin-4（3H）-one合成的。通过分析和光谱数
• Synthetic approaches to bridgehead nitrogen methanesulfonamide derivatives of 3-amino-2-thioxo-2,3-dihydrothieno[2,3-<i>d</i>]pyrimidin-4(1<i>H</i>)-ones, potential cox-2 selective inhibitors
  作者：Giuseppe Granata、Salvatore Barbagallo、Antonio Perdicaro、Agostino Marrazzo、Andrea Santagati、Laura Lombardo、Venera Cardile

  DOI：10.1002/jhet.5570430443

  日期：2006.7

  Methane sulfonamide derivatives of 3-amino-2-thioxo-2,3-dihydrothieno[2,3-d]pyimidin-4(1H)-one, potential selective COX-2 inhibitors, were synthesized and their structural elucidation is here reported. Some derivatives, at 10 μM concentration, showed a significant percentage of inhibition in some in vitro experiments.

  合成了3-氨基-2-硫代-2,3-二氢噻吩并[2,3- d ]嘧啶-4（1 H）-一的甲烷磺酰胺衍生物，一种潜在的选择性COX-2抑制剂，并在此报道了其结构解析。在某些体外实验中，浓度为10μM的某些衍生物显示出显着的抑制百分比。
• COMPOUND FOR INHIBITING THE GROWTH AND PROLIFERATION OF HUMAN LIVER CANCER CELLS AND METHOD FOR SYNTHESIZING IT
  申请人：Alghamdi Zainab Saeed

  公开号：US20160280717A1

  公开（公告）日：2016-09-29

  The compound “2-((4-nitrophenyl)amino)-6,7,8,9-tetrahydro-3H-cyclohepta[4,5]thieno-[2,3-d]pyrimidin-4(5H)-one” and method of synthesizing it, wherein the compound is effective to inhibit the growth and proliferation of human liver cancer cells HepG2. The compound has an inhibitory concentration value (IC 50 ) of 0.7 μg, compared to reference medication Doxorubicin that has an (IC 50 ) value of 1.2 μg. It further surpasses that reference medication Doxorubicin at all tested concentraions. The method includes the steps of: preparing a first compound of cycloheptanone, ethylcyanoacetate, sulfur, ethanol and diethyl amine; preparing a second compound by heating of the first compound with excess of hydrazine hydrate in absolute ethanol as solvent; and preparing the effective compound of the invention by reaction of the second chemical compound with 4-nitrophenylisothiocyanate in dry dimethylformamide as solvent.

  这个化合物“2-((4-硝基苯基)氨基)-6,7,8,9-四氢-3H-环庚并[4,5]噻吩-[2,3-d]嘧啶-4(5H)-酮”及其合成方法，其中该化合物有效抑制人肝癌细胞HepG2的生长和增殖。该化合物的抑制浓度值（IC50）为0.7微克，而参考药物多柔比星的IC50值为1.2微克。在所有测试浓度下，它进一步超越了参考药物多柔比星。该方法包括以下步骤：准备环庚酮、氰乙酸乙酯、硫、乙醇和二乙胺的第一化合物；通过在绝对乙醇中过量加热第一化合物与水合肼的第二化合物；通过在干二甲基甲酰胺中与4-硝基苯基异硫氰酸酯反应制备本发明的有效化合物。
• COMPOUND FOR THE TREATMENT OF HUMAN LIVER CANCER AND METHOD FOR SYNTHESIZING IT
  申请人：Alghamdi Zainab Saeed

  公开号：US20160200740A1

  公开（公告）日：2016-07-14

  The compound “2-((4-nitrophenyl)amino)-7,8,9,10-tetrahydro cyclohepta[4,5]thieno[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidin-11(6H)-one” and method of synthesizing it, wherein the compound is effective to inhibit the growth and proliferation of human liver cancer cells HepG2. The compound has a higher efficiency to inhibit the growth and proliferation of these cells as it has an inhibitory concentration value (IC 50 ) of 0.7 μg, compared to reference medication Doxorubicin that has an (IC 50 ) value of 1.2 μg. It further surpasses that reference medication at all tested concentrations. The method includes the steps of: preparing a first compound of cycloheptanone, ethylcyanoacetate, sulfur, ethanol and diethylamine; preparing a second compound by heating of the first compound with excess of hydrazine hydrate in absolute ethanol as solvent; preparing a third compound by heating the second compound with carbon disulphide in dry pyridine; and preparing the compound of the invention by reacting the third compound with 4-nitrophenylisothiocyanate in dry N,N-methylformamide as solvent.

  这个化合物是“2-((4-硝基苯基)氨基)-7,8,9,10-四氢环庚并[4,5]噻吩[2,3-d][1,3,4]噻二唑并[3,2-a]嘧啶-11(6H)-酮”，以及合成它的方法，其中这个化合物有效地抑制人类肝癌细胞HepG2的生长和增殖。与参考药物多柔比星（Doxorubicin）的IC50值为1.2μg相比，该化合物具有更高的效率来抑制这些细胞的生长和增殖，其IC50值为0.7μg。它在所有测试浓度下进一步超越了参考药物。该方法包括以下步骤：制备环庚酮、乙基氰乙酸酯、硫、乙醇和二乙胺的第一化合物；通过在绝对乙醇中用过量的水合肼加热第一化合物制备第二化合物；通过在干燥吡啶中用二硫化碳加热第二化合物制备第三化合物；通过在干燥N,N-甲基甲酰胺中用4-硝基苯基异硫氰酸酯与第三化合物反应制备该发明的化合物。