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3-amino-5-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester | 304898-07-5

中文名称
——
中文别名
——
英文名称
3-amino-5-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester
英文别名
3-amino-6-carbethoxy-2,3-dihydro-5-methyl-2-thioxothieno[2,3-d]pyrimidin-4(1H)-one;3-amino-6-carboxyethyl-5-methyl-2-thioxo-thieno[2,3-d]pyrimidin-4-one;Ethyl 3-amino-5-methyl-4-oxo-2-sulfanylidene-1H,2H,3H,4H-thieno[2,3-D]pyrimidine-6-carboxylate;ethyl 3-amino-5-methyl-4-oxo-2-sulfanylidene-1H-thieno[2,3-d]pyrimidine-6-carboxylate
3-amino-5-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester化学式
CAS
304898-07-5
化学式
C10H11N3O3S2
mdl
MFCD15089934
分子量
285.348
InChiKey
PCJUWTVHSALLEP-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.4
  • 重原子数:
    18
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.3
  • 拓扑面积:
    145
  • 氢给体数:
    2
  • 氢受体数:
    6

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    3-amino-5-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester一水合肼 作用下, 以 乙醇 为溶剂, 反应 8.0h, 以79%的产率得到3-amino-5-methyl-4-oxo-2-hydrazino-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-yl hydrazide
    参考文献:
    名称:
    一些新的硫杂环化合物作为潜在的辐射防护和抗癌剂的合成
    摘要:
    一些新型 5-取代氨基-3-甲基噻吩-2,4-二羧酸二乙酯 (3-6), 3,5-二甲基-4-氧代-2-硫代-1,2,3,4-四氢-噻吩并 [2,3-d] 嘧啶 (7)、咪唑并噻吩并嘧啶 (8) 和 1,2,4-三唑并噻吩并嘧啶 (11) 通过异硫氰酸酯 2 与不同试剂的反应合成。新化合物的鉴定是通过元素分析、IR、1H NMR 和质谱数据确定的。测试了一些制备的化合物的辐射防护和抗癌活性。化合物 7 和 16 显示出显着的抗 EAC 细胞活性,而化合物 5 显示出辐射防护活性。
    DOI:
    10.1080/10426500500544014
  • 作为产物:
    参考文献:
    名称:
    一些新的硫杂环化合物作为潜在的辐射防护和抗癌剂的合成
    摘要:
    一些新型 5-取代氨基-3-甲基噻吩-2,4-二羧酸二乙酯 (3-6), 3,5-二甲基-4-氧代-2-硫代-1,2,3,4-四氢-噻吩并 [2,3-d] 嘧啶 (7)、咪唑并噻吩并嘧啶 (8) 和 1,2,4-三唑并噻吩并嘧啶 (11) 通过异硫氰酸酯 2 与不同试剂的反应合成。新化合物的鉴定是通过元素分析、IR、1H NMR 和质谱数据确定的。测试了一些制备的化合物的辐射防护和抗癌活性。化合物 7 和 16 显示出显着的抗 EAC 细胞活性,而化合物 5 显示出辐射防护活性。
    DOI:
    10.1080/10426500500544014
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文献信息

  • Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents
    作者:Hend N. Hafez、Abdel-Rahman B.A. El-Gazzar、Galal A.M. Nawwar
    DOI:10.1016/j.ejmech.2009.12.056
    日期:2010.4
    Several 2-thioglycosides were prepared. Glycosylation of 2-thioxo-thieno[2,3-d]-pyrimidines 5a,b with 1-bromo-2,3,5-tri-O-acetyl-alpha-D-arabinofuranosyle 7, 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl and galacto-pyranosyl bromide 8a,b gave the protected beta-n-nuclosides 10a,b and 13a-d in high yields, which were transformed to deacetylated derivatives 14a,b and 15a-d. The structures of the compounds were elucidated by spectral and elemental analysis. Anti-inflammatory and Analgesic activities screening of the new compounds (at a dose of 100 mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method exhibited that the deacetylated derivatives 14a,b and 15a-d possess highly promising activities. (C) 2010 Elsevier Masson SAS. All rights reserved.
  • High affinity and selectivity of [[(arylpiperazinyl)alkyl]thio]thieno[2,3-d]pyrimidinone derivatives for the 5-HT1A receptor.Synthesis and structure–affinity relationships
    作者:Maria Modica、Maria Santagati、Filippo Russo、Carlo Selvaggini、Alfredo Cagnotto、Tiziana Mennini
    DOI:10.1016/s0223-5234(00)00175-6
    日期:2000.8
    In this work we report the affinity of new thienopyrimidinones for 5-HT(1A)Rs and the selectivity versus alpha(1)ARs. The 3-amino-2-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]thio]-6-ethyl-thieno[2,3-d]pyrimidin-4(3H)-one 27 is the most potent and selective (Ki 0.19 nM, selectivity 115). Compound 31 with the N4 piperazine orthonitrophenyl nucleus instead of the orthomethoxyphenyl also shows a good affinity and selectivity (Ki 1.46 nM, selectivity 84). The results of derivatives 28, 29 and 30 (Ki 3.28, 12.59 and 4.38 nM; selectivity 24, 4 and 5, respectively), which have, respectively, an ethyl, an allyl and an acetylamino group instead of an N3 amino group, indicate the importance of this last group for the interaction with 5-HT1AR. Comparison of the results for the superior homologue 53 (Ki 3.72 nM, selectivity 51) and the inferior homologue 52 (5-HT1A Ki 1 499 nM, alpha(1)A Ki NA) of 2-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-6,7-dimethyl-8H-[1,3,4]thiadiazolo[3,2-a]thieno[2,3-d]pyrimidin-8-one 57 (Ki 23 nM, selectivity 5) shows how important the length of the chain binding the two heterocyclic systems is in the interaction with 5-HT(1A)Rs and alpha(1)ARs. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
  • Design and synthesis of 3-pyrazolyl-thiophene, thieno[2,3-d]pyrimidines as new bioactive and pharmacological activities
    作者:H.N. Hafez、A.B.A. El-Gazzar
    DOI:10.1016/j.bmcl.2008.08.071
    日期:2008.10
    Two series of 5-ethyl-2-amino-3-pyrazolyl-4- methylthiophenecarboxylate and 2-thioxo-N-3-aminothieno[ 2,3-d]pyrimidines were prepared from 3,5-diethyl-2-amino-4-methylthio-phenecaboxylate and evaluated as anti-inflammatory, analgesic and ulcerogenic activities. Among the compounds studied, compounds which containing the substituted hydrazide at C-3 position 7, 16, and 17a showed more potent anti-inflammatory and analgesic activities than the standard drug (Indomethacin and Aspirin), along without ulcerogenity. While compounds 2, 5, 9, 10, and 11c showed moderate activities. Some of the newly synthesized compounds have good to excellent antimicrobial activity. (C) 2008 Elsevier Ltd. All rights reserved.
  • The Synthesis of Some New Sulfur Heterocyclic Compounds as Potential Radioprotective and Anticancer Agents
    作者:M. M. Ghorab、A. N. Osman、E. Noaman、H. I. Heiba、N. H. Zaher
    DOI:10.1080/10426500500544014
    日期:2006.8.1
    reagents. The identification of the new compounds was established by elemental analysis, and IR, 1H NMR, and mass spectral data. Some prepared compounds were tested for their radioprotective and anticancer activities. Compounds 7 and 16 showed significant activities against EAC cells, while compound 5 exhibited radioprotective activity.
    一些新型 5-取代氨基-3-甲基噻吩-2,4-二羧酸二乙酯 (3-6), 3,5-二甲基-4-氧代-2-硫代-1,2,3,4-四氢-噻吩并 [2,3-d] 嘧啶 (7)、咪唑并噻吩并嘧啶 (8) 和 1,2,4-三唑并噻吩并嘧啶 (11) 通过异硫氰酸酯 2 与不同试剂的反应合成。新化合物的鉴定是通过元素分析、IR、1H NMR 和质谱数据确定的。测试了一些制备的化合物的辐射防护和抗癌活性。化合物 7 和 16 显示出显着的抗 EAC 细胞活性,而化合物 5 显示出辐射防护活性。
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林扎戈利 替普司特 噻吩并[3,4-d]嘧啶-2,4(1H,3H,5H,7H)-二酮 噻吩并[3,2-d]嘧啶-7-甲胺 噻吩并[3,2-d]嘧啶-4-羧酸 噻吩并[3,2-d]嘧啶-4(1H)-硫酮 噻吩并[3,2-d]嘧啶,4-(甲硫基)- 噻吩并[3,2-d]嘧啶 噻吩并[3,2-D]嘧啶-7-羧酸 噻吩并[3,2-D]嘧啶-7-甲醛 噻吩并[3,2-D]嘧啶-7-基甲醇 噻吩并[3,2-D]嘧啶-2-胺 噻吩并[2,3-d]嘧啶-4-胺 噻吩并[2,3-d]嘧啶-4-硫醇 噻吩并[2,3-d]嘧啶-4(3H)-酮 噻吩并[2,3-d]嘧啶-2,4-二胺 噻吩并[2,3-d]嘧啶-2,4(1H,3H)-二酮,3-(3-甲氧苯基)-6-(4-甲氧苯基)-5-甲基- 噻吩并[2,3-d]嘧啶-2,4(1H,3H)-二酮,3-(3-氯苯基)-1-[(2,6-二氟苯基)甲基]-6-(4-甲氧苯基)-5-甲基- 噻吩并[2,3-d]嘧啶-2,4(1H,3H)-二酮,3-(2-氯苯基)-1-[(2,6-二氟苯基)甲基]-6-(4-甲氧苯基)-5-甲基- 噻吩并[2,3-d]嘧啶 噻吩并[2,3-D]嘧啶-6-羧酸 噻吩并[2,3-D]嘧啶-6-甲醛 吡啶并[3’,2’:4,5]噻吩并[3,2-d]嘧啶-4(3h)-酮 乙基3-甲基-5-羰基-5H-[1]苯并噻吩并[2,3-d][1,3]噻唑并[3,2-a]嘧啶-2-羧酸酯 乙基2-(4-氯苯基)-7-甲基-9-羰基-9H-[1,3]噻唑并[3,2-a]噻吩并[3,2-d]嘧啶-6-羧酸酯 {[((4-氧代-3,4,5,6,7,8-六氢[1]苯并噻吩并[2,3-d]嘧啶-2-基)甲基]硫基}乙酸 [(6-甲基噻吩并[2,3-d]嘧啶-4-基)硫基]乙酸 [(4-氧代-3,4,5,6,7,8-六氢[1]苯并噻吩并[2,3-d]嘧啶-2-基)硫基]乙酸 PI3K抑制剂 PF-3758309抑制剂 Necrostatin-5; 2-[[3,4,5,6,7,8-六氢-3-(4-甲氧基苯基)-4-氧代[1]苯并噻吩并[2,3-d]嘧啶-2-基]硫代]-乙腈 N-甲基-1-噻吩并[3,2-d]嘧啶-4-基-4-哌啶甲胺 N-[2-[[3,4-二氢-4-氧代-3-[4-(2,2,2-三氟乙氧基)苯基]噻吩并[3,4-d]嘧啶-2-基]硫基]乙基]乙酰胺 N-[(1S)-2-(二甲基氨基)-1-苯基乙基]-2,6-二氢-6,6-二甲基-3-[(2-甲基噻吩并[3,2-d]嘧啶-4-基)氨基]-吡咯并[3,4-c]吡唑-5(4H)-甲酰胺盐酸盐 N-(6-甲基-2-苯并噻唑基)-2-[(3,4,6,7-四氢-3-(2-甲氧基苯基)-4-氧噻吩并[3,2-d]嘧啶-2-基)硫代]-乙酰胺 N-(4-氟苯基)-5,6-二甲基噻吩并[2,3-D]嘧啶-4-胺 N-(4-吗啉-4-基噻吩并[2,3-e]嘧啶-2-基)乙烷-1,2-二胺 N,N-二甲基-5,6,7,8-四氢苯并[4,5]噻吩并[2,3-D]嘧啶-4-胺 IWP2;N-(6-甲基-2-苯并噻唑基)-2-[(3,4,6,7-四氢-4-氧代-3-苯基噻吩并[3,2d]嘧啶-2-基)硫基]乙酰胺 AR-C 155858; (S)-6-[(3,5-二甲基-1H-吡唑-4-基)甲基]-5-[(4-羟基异噁唑烷-2-基)羰基]-1-异丁基-3-甲基噻吩并[2,3-d]嘧啶-2,4(1H,3H)-二酮 7-甲基噻吩并[3,2-D]嘧啶-4-胺 7-甲基-噻吩并[3,2-d]嘧啶-2,4(1h,3h)-二酮 7-甲基-噻吩并[3,2-d]嘧啶 7-甲基-5,6,7,8-四氢[1]苯并噻吩并[2,3-d]嘧啶-4(3h)-酮 7-甲基-5,6,7,8-四氢-苯并[4,5]噻吩并[2,3-d]嘧啶-4-硫醇 7-溴噻吩并[3,2-d]嘧啶 7-溴噻吩并[3,2-D]嘧啶-4(1H)-酮 7-溴-噻吩并[3,2-d]嘧啶-4-胺 7-溴-4-氯噻酚并[3,2-D]嘧啶 7-溴-2-氯噻吩并[3,2-D]嘧啶