1,2-二氢-2-(硫代)-5-(3-苯基-2-丙烯-1-亚基)嘧啶-4,6(3H,5H)-二酮 | 27430-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1,2-二氢-2-(硫代)-5-(3-苯基-2-丙烯-1-亚基)嘧啶-4,6(3H,5H)-二酮
• 英文名称: 5-(3-phenylallylidene)-2-thioxodihydropyrimidine-4,6-dione
• 英文别名: (E)-5-(3-phenylallylidene)-2-thioxodihydropyrimidine-4,6-dione；5-trans-cinnamylidene-2-thio-barbituric acid；5-cinnamylidene-2-thio-barbituric acid；5-trans-Cinnamyliden-2-thio-barbitursaeure；5-Cinnamyliden-2-thio-barbitursaeure；5-[(E)-3-phenylprop-2-enylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 27430-17-7
• 化学式: C₁₃H₁₀N₂O₂S
• 分子量: 258.301
• InChiKey: JGXUXEILGGWPJR-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 4,6-二羟基-2-巯基嘧啶 以 水 为溶剂， 反应 1.0h， 以89%的产率得到1,2-二氢-2-(硫代)-5-(3-苯基-2-丙烯-1-亚基)嘧啶-4,6(3H,5H)-二酮
  参考文献：
  名称：

  Synthesis of barbiturate-based methionine aminopeptidase-1 inhibitors

  摘要：

  The syntheses of a new class of barbiturate-based inhibitors for human and Escherichia Coli methionine aminopeptidase-1 (MetAP-1) are described. Some of the synthesized inhibitors show selective inhibition of the human enzyme with high potency. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.066

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。
• Barbituric acid analogs as therapeutic agents
  申请人：——

  公开号：US20030229108A1

  公开（公告）日：2003-12-11

  This invention pertains to active barbituric acid analogs which inhibit HIF-1 activity (e.g., the interaction between HIF-1&agr; and p300) and thereby inhibit angiogenesis, tumorigensis, and proliferative conditions, such as cancer. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HIF-1 activity, and to inhibit angiogensis, tumorigensis, and proliferative conditions, such as cancer.

  这项发明涉及活性巴比妥酸类似物，其抑制HIF-1活性（例如，HIF-1α与p300之间的相互作用），从而抑制血管生成、肿瘤发生和增生性疾病，如癌症。本发明还涉及包括这些化合物的药物组合物，以及在体外和体内使用这些化合物和组合物来抑制HIF-1活性，以及抑制血管生成、肿瘤发生和增生性疾病，如癌症。
• A study on the physical properties of low melting mixtures and their use as catalysts/solvent in the synthesis of barbiturates
  作者：Letcy Vincent Theresa、Govindan Avudaiappan、Machingal Shaibuna、Kottayil Hiba、Krishnapillai Sreekumar

  DOI：10.1002/jhet.4315

  日期：2021.9

  In recent years, deep eutectic solvents have become attractive due to their interesting characteristics such as, physicochemical properties, low cost of components, easiness to prepare, low toxicity, bio-renewability, and biodegradability. In order to make the deep eutectic mixture more cost-effective and renewable, carbohydrate derivatives were linked with deep eutectic mixtures, since, carbohydrates

  近年来，深共熔溶剂由于其物理化学性质、组分成本低、易于制备、低毒性、生物可再生和生物降解性等有趣特性而变得有吸引力。为了使深共晶混合物更具成本效益和可再生性，碳水化合物衍生物与深共晶混合物相关联，因为碳水化合物是地球上最重要和分布最广的可再生化合物。在这项工作中，我们使用由碳水化合物组成的低熔点混合物来创建有机转化的反应介质。对混合物的密度、粘度、酸度、折射率、表面张力、溶解度、玻璃化转变温度、热稳定性、溶剂极性和毒性等物理性质进行了研究。低熔点混合物被用作反应介质和催化剂以有效合成巴比妥酸盐。醛类与巴比妥酸/硫代巴比妥酸之间的反应，以及醛类、巴比妥酸/硫代巴比妥酸和丙二腈/二甲酮之间的反应均以良好到极好的收率进行。还确定了催化剂/溶剂的可回收性。
• 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。
• Design and synthesis of novel thiobarbituric acid derivatives targeting both wild-type and BRAF-mutated melanoma cells
  作者：Srinivasa Rao Ramisetti、Manoj K. Pandey、Sang Y. Lee、Deepkamal Karelia、Satya Narayan、Shantu Amin、Arun K. Sharma

  DOI：10.1016/j.ejmech.2017.11.006

  日期：2018.1

  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.