N-乙基-N'-2-丙烯-1-基-硫脲 | 32900-09-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫脲类
• 中文名称: N-乙基-N'-2-丙烯-1-基-硫脲
• 英文名称: N-allyl-N'-ethylthiourea
• 英文别名: N-ethyl-N'-allyl-thiourea；N-Aethyl-N'-allyl-thioharnstoff；1-allyl-3-ethylthiourea；1-ethyl-3-prop-2-enylthiourea
• CAS: 32900-09-7
• 化学式: C₆H₁₂N₂S
• mdl: MFCD00046854
• 分子量: 144.241
• InChiKey: MMNIUSWSBKDYQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-乙基-N'-2-丙烯-1-基-硫脲 在 吡啶 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 1-allyl-3-ethyl-5-(3-furan-2-ylallylidene)-2-thioxodihydropyrimidine-4,6-dione
  参考文献：
  名称：

  Design and synthesis of novel thiobarbituric acid derivatives targeting both wild-type and BRAF-mutated melanoma cells

  摘要：

  A series of novel thio-and seleno-barbituric acid derivatives were synthesized by varying the substituents at N1 and N3 (ethyl, methyl, allyl, and phenyl), and C5 tethered with dienyl and trienyl moieties attached to substituents such as phenyl, 2-furanyl, 2-thiophenyl, l-naphthyl, and 3-pyridyl. The cytotoxic potential of these derivatives was evaluated by using MTT assay against melanoma cell lines expressing either wild-type (CHL-1) or mutant (UACC 903) BRAF gene. Among all, 2b and 8b were identified as the most potent compounds. Both 2b and 8b inhibited viability of various melanoma cells and induced cell death as evidenced by Live and Dead assay. Western blot analysis showed that they induce PARP cleavage and inhibit anti-apoptotic Bcl-2, Bcl-xL and Survivin in a dose-dependent manner within 24 h of the treatment. Novel thiobarbituric acid analogs also inhibited viability of various other solid tumor cell lines, such as pancreatic, breast, and colon. Overall, 2b, 2d, and 8b emerged as the most effective compounds and make good leads for the development of future therapeutic agents. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.006
• 作为产物：
  描述：

  异硫氰酸乙酯 、 丙烯胺 生成 N-乙基-N'-2-丙烯-1-基-硫脲
  参考文献：
  名称：

  Hecht, Chemische Berichte, 1890, vol. 23, p. 286

  摘要：

  DOI：

文献信息

• [EN] COMPOUNDS FOR USE IN CANCER THERAPY<br/>[FR] COMPOSÉS POUR UTILISATION DANS LA THÉRAPIE DU CANCER
  申请人：NUHOPE LLC

  公开号：WO2013024447A1

  公开（公告）日：2013-02-21

  Provided are methods and compositions for use in therapy, and in particular for treating cancer, preferably drug-resistant cancer, and/or radiation resistant cancer. The compounds may be used for reducing tumor size in a mammalian subject and for inducing apoptosis in a tumor cell. The methods are effective on tumor cells that are resistant to drugs such as temozolomide, doxorubicin, and geldanamycin, as well as non-resistant tumor cells. Further provided are barbiturate and thiobarbiturates diene compounds for use in treating cancer, and uses, methods and compositions relating to these compounds.

  提供了用于治疗的方法和组合物，特别是用于治疗癌症，最好是药物耐药性癌症和/或放射线耐药性癌症。这些化合物可用于减小哺乳动物主体的肿瘤大小，并诱导肿瘤细胞凋亡。这些方法对于对于药物如替莫唑胺、多柔比星和格兰达霉素耐药的肿瘤细胞以及非耐药的肿瘤细胞都有效。此外，还提供了用于治疗癌症的巴比妥和硫代巴比妥二烯化合物，以及与这些化合物相关的用途、方法和组合物。
• Synthesis of Alkyl- and Phenyl-2-thiouracils and 1,3-Thiazin-4-ones by Nucleophilic Substitution of Unsymmetrical Thioureas with 3-Chloropropenoates
  作者：Lars F. Jalander、Jan-Erik Lönnqvist

  DOI：10.1135/cccc19991307

  日期：——

  Unsymmetrically substituted thioureas and ethyl (E)- and (Z)-3-aryl-3-chloro-2-cyano- propenoates (1a) and (1b) gave after nucleophilic vinylic substitution and cyclisation two isomers of 1,3-disubstituted 6-aryl-5-cyano-2-thiouracil derivatives, 3a-3i and 4a-4i. Substituted 1,3-thiazin-4-ones 5a-5d were formed in moderate to good yields when monosubstituted thioureas were allowed to react under similar conditions.

  非对称取代硫脲和乙基（E）-和（Z）-3-芳基-3-氯-2-氰基丙烯酸乙酯（1a）和（1b）在亲核乙烯取代和环化后形成了1,3-二取代6-芳基-5-氰基-2-硫脲衍生物的两个异构体，3a-3i和4a-4i。当单取代硫脲在类似条件下反应时，取代的1,3-噻唑-4-酮5a-5d以中等至良好的产率形成。
• COMPOUNDS FOR USE IN CANCER THERAPY
  申请人：Connor James R.

  公开号：US20150065531A1

  公开（公告）日：2015-03-05

  Provided are methods and compositions for use in therapy, and in particular for treating cancer, preferably drug-resistant cancer, and/or radiation resistant cancer. The compounds may be used for reducing tumor size in a mammalian subject and for inducing apoptosis in a tumor cell. The methods are effective on tumor cells that are resistant to drugs such as temozolomide, doxorubicin, and geldanamycin, as well as non-resistant tumor cells. Further provided are barbiturate and thiobarbiturates diene compounds for use in treating cancer, and uses, methods and compositions relating to these compounds.

  提供了用于治疗疾病的方法和成分，特别是用于治疗癌症，优选为耐药性癌症和/或放射线耐药性癌症。这些化合物可用于减小哺乳动物主体的肿瘤大小，并诱导肿瘤细胞凋亡。这些方法对于耐药性药物如替莫唑胺、多柔比星和格尔达纳霉素以及非耐药性肿瘤细胞都有效。此外，还提供了用于治疗癌症的巴比妥和硫代巴比妥二烯化合物，以及与这些化合物相关的用途、方法和组合物。
• Forster, Justus Liebigs Annalen der Chemie, 1875, vol. 175, p. 32
  作者：Forster

  DOI：——

  日期：——
• Avenarius, Chemische Berichte, 1891, vol. 24, p. 269
  作者：Avenarius

  DOI：——

  日期：——