N-allyl-2-thiobarbituric acid | 65960-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-allyl-2-thiobarbituric acid
• 英文别名: 1-allyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione；1-Prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 65960-00-1
• 化学式: C₇H₈N₂O₂S
• 分子量: 184.219
• InChiKey: TZQUCJIOQVUZIZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-噻吩基)-2-丙烯醛 、 N-allyl-2-thiobarbituric acid 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以82%的产率得到1-allyl-5-(3-thiophen-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：

  1-allyl-6-amino-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 在 硫酸 作用下， 生成 N-allyl-2-thiobarbituric acid
  参考文献：
  名称：

  L'acide p-Diméthylaminobenzylidènethiobarbiturique et ses dérivés dans la recherche des métaux nobles

  摘要：

  DOI：

  10.1016/s0003-2670(00)87305-5

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 and antimicrobial evaluation of the novel heteroannulated furo[3′,2′:6,7]chromeno[2,3‐b]pyridines: Part 1
  作者：Magdy A. Ibrahim、Sami A. Al‐Harbi、Esam S. Allehyani

  DOI：10.1002/jhet.4082

  日期：2020.10

  The chemical behavior of 4,9‐dimethoxy‐5‐oxo‐5H‐furo[3,2‐g]chromene‐6‐carbonitrile (1) was investigated toward some acyclic and cyclic active methylene ketones namely acetylacetone, ethyl acetoacetate, ethyl benzoylacetate, acetoacetanilide, dimedone, indanedione, pyrazolidine‐3,5‐dione and 5‐methyl‐2‐phenyl‐2,4‐dihydro‐3H‐pyrazol‐3‐one, barbituric acid and 1‐allylthiobarbituric acid, and hippuric

  研究了4,9-二甲氧基-5-氧代-5 H-呋喃[3,2 - g ]亚甲基-6-腈（1）对一些无环和环状活性亚甲基酮的反应，即乙酰丙酮，乙酰乙酸乙酯，乙基苯甲酰乙酸，乙酰乙酰苯胺，二甲酮，茚二酮，吡唑烷-3-，5-二酮和5-甲基-2-苯基-2-，4-二氢-3 H-吡唑-3-酮，巴比妥酸和1-烯丙基硫代巴比妥酸和马尿酸。通过4,9-二甲氧基-5-氧代-5 H-呋喃[3,2 - g ]色烯-6-腈（1的级联反应）有效地合成了多种新型的异环呋喃铬吡啶）和碳亲核试剂。根据新产品的分析和光谱数据推断其结构。
• Chemical behavior of 4, <scp>9‐dimethoxy‐5‐oxo‐5</scp> <i>H</i> ‐furo[3,2‐ <i>g</i> ]chromene‐6‐carboxaldehyde towards carbon nucleophilic reagents
  作者：Magdy A. Ibrahim、Nasser M. El‐Gohary

  DOI：10.1002/jhet.3991

  日期：2020.7

  4‐dihydro‐3H ‐pyrazol‐3‐one proceeds in 1:2 M ratio producing pyrazolo [4′,3′:5,6]pyrano[2,3‐c ]pyrazole derivative 22 . Carboxaldehyde 1 reacted with certain heterocyclic compounds containing active methylene groups to give the corresponding condensation products 22 ‐27 . The synthesized compounds were screened in vitro for their antimicrobial activity and showed high to moderate activities against the tested

  研究了6-甲酰基khellin（1）对多种碳亲核试剂的化学行为。用氰基乙酰胺处理醛1，N-苄基氰基乙酰胺生成吡啶3-羧酰胺3和4。用丙二腈二聚体和1 H-苯并咪唑-2-基乙腈处理甲醛1分别得到1,6-萘并吡啶5和吡啶并[1,2- a ]苯并咪唑6。一些新颖的吡唑并[3,4- b ]吡啶7，吡啶并[2,3- d ]嘧啶8和9由羧醛1与某些杂环烯胺的开环闭环反应合成。另外，羧醛1与某些环状烯醇的反应产生了多种产物。用1,3-环己二酮处理甲醛1可以得到an吨-1,8-二酮19和20。甲醛1与5-甲基-2,4-二氢-3 H-吡唑-3-酮的反应以1：2 M的比例进行，生成吡唑并[4'，3'：5,6]吡喃并[2,3- c ]吡唑衍生物22。甲醛1与含有活性亚甲基，得到相应的缩合产物某些杂环化合物反应22 - 27。体外筛选了合成的化合物的抗微生物活性，并显示了对测试微生物的高至中等活性。
• [EN] 2-CARBAMO(THIO)YL-1,3- DIOXOPROPYL DERIVATIVES IN CANCER THERAPY<br/>[FR] DÉRIVÉS 2-CARBAMO(THIO)YL-1,3-DIOXOPROPYLÉS EN THÉRAPIE DU CANCER
  申请人：CHEE GAIK-LEAN

  公开号：WO2013159224A1

  公开（公告）日：2013-10-31

  Certain 2-carbamo(thio)yl-1,3-dioxopropyl derivatives, or the tautomers and pharmacologically acceptable addition salts thereof are found to be toxic to cancer cells, in part, by inhibiting DNA topoisomerase II enzyme making them candidates for pharmaceutical use as anticancer agents.

  已发现某些2-氨基甲酰基(硫)基-1,3-二氧代丙基衍生物，或其互变异构体和药理学上可接受的加合盐对癌细胞具有毒性，部分原因是通过抑制DNA拓扑异构酶II酶来使它们成为抗癌药物的候选药物。
• Ring Opening and Recyclization Reactions with Chromone‐3‐carbonitrile
  作者：Magdy A. Ibrahim、Azza M. El‐Kazak

  DOI：10.1002/jhet.3495

  日期：2019.3

  transformations of chromone‐3‐carbonitrile (1) with some substituted hydrazines, namely, thiosemicarbazide, S‐methyl/benzyldithiocarbazate, 7‐chloro‐4‐hydrazinoquinoline, and 3‐hydrazino‐5,6‐diphenyl‐1,2,4‐triazine, led to substituted pyrazoles 2, 5–8. Ring opening of carbonitrile 1 followed by recyclization with 3‐amino‐1,2,4‐triazole and 2‐aminobenzimidazole gave triazolo[1,5‐a]pyrimidine 9 and pyrimido[1,2‐a]benzimidazole

  色酮3-腈（1）与一些取代的肼的化学转化，即硫代氨基脲，S-甲基/苄基二硫代氨基甲酸酯，7-氯-4-肼基喹啉和3-肼基-5-6,6-二苯基-1,2.4嗪，导致取代的吡唑2，5 - 8。腈1的开环，然后用3-氨基1,2,4-三唑和2-氨基苯并咪唑进行环化，分别得到三唑并[1,5- a ]嘧啶9和嘧啶基[1,2- a ]苯并咪唑10。用一些杂环胺处理腈1会生成2-氨基3-取代的色酮11和12。新型的3-羟基色酚[4,3- b ]吡唑并[4,3 - e ]吡啶-5（1 H）-one（13）是由腈1与氰基乙酰肼进行环转化而有效合成的。由丙二腈1与丙二腈二聚体进行碱催化转化获得了铬诺[2,3- b ]萘啶14和铬诺[4,3- b ]吡啶15的混合物。新颖稠色烯并[2,3-的多样性b〕吡啶16 - 22也被合成。Chromeno [2,3‐ b]吡咯-2-羧酸酯23是由腈1与氯乙酸乙酯反应制得的。根据新合成产物的分析和光谱数据推导其结构。