(2-chloro-6-fluoro-benzylidene)aminoguanidine | 46275-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-chloro-6-fluoro-benzylidene)aminoguanidine
• 英文别名: N-{[(2-chloro-6-fluorophenyl)methylidene]amino}guanidine；2-[(2-chloro-6-fluorophenyl)methylideneamino]guanidine
• CAS: 46275-12-1
• 化学式: C₈H₈ClFN₄
• mdl: MFCD05487819
• 分子量: 214.63
• InChiKey: VOHVPEXIOIAMMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-chloro-6-fluoro-benzylidene)aminoguanidine 以 甲醇 、 乙腈 为溶剂， 生成 methyl 2-(2-((N''-(2-chloro-6-fluorobenzylidene)carbamohydrazonoyl)imino)-3-(3-methoxyphenyl)-4-oxothiazolidin-5-ylidene)acetate
  参考文献：
  名称：

  Antiproliferative activity and molecular docking studies of new 4-oxothiazolidin-5-ylidene acetate derivatives containing guanylhydrazone moiety

  摘要：

  DOI：

  10.1016/j.molstruc.2022.132627
• 作为产物：
  描述：

  2-氯-6-氟-苯甲醛 、 肼甲酰亚胺酰胺一氯化氢 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以87%的产率得到(2-chloro-6-fluoro-benzylidene)aminoguanidine
  参考文献：
  名称：

  Synthesis of Conjugates of 6-Aminophenanthridine and Guanabenz, Two Structurally Unrelated Prion Inhibitors, for the Determination of Their Cellular Targets by Affinity Chromatography

  摘要：

  The synthesis of affinity matrices for 6-aminophenanthridine (6AP) and 2,6-dichlorobenzylidenaminoguanidine (Guanabenz, GA), two unrelated prion inhibitors, is described. In both cases, the same simple spacer, epsilon-aminocaproylaminopentanol, was introduced by a Mitsunobu reaction and the choice of the anchoring position of the linker was determined by the study of the residual antiprion activity of the corresponding 6AP or GA conjugates. Very recently, these two affinity matrices were used for chromatography assays leading to the identification of ribosome (via the rRNA) as a common target of these two antiprion drugs. Here, we show, using competition experiments with Quinacrine (QC) and Chlorpromazine (CPZ), two other antiprion drugs, that QC, but not CPZ, may also directly target the rRNA.

  DOI：

  10.1021/bc900314n

文献信息

• Efficient synthesis and molecular docking studies of new pyrimidine-chromeno hybrid derivatives as potential antiproliferative agents
  作者：Sevtap Çağlar Yavuz、Senem Akkoç、Burak Tüzün、Onur Şahin、Emin Saripinar

  DOI：10.1080/00397911.2021.1922920

  日期：2021.7.18

  Abstract Various novel heterocyclic compounds containing pyrimidine nuclei 5H-chromeno[4,3-d]pyrimidine (4a–c, e–h, l–r, t) and pyrimidine-5-yl-(2-hydroxyphenyl)methanone (5a, c, d, f–k, m–o, r, s, u) were synthesized from the reaction of guanylhydrazones (2a–u) and 3-formylchromone (3). These compounds were tested against human liver hepatocellular carcinoma cell line (HepG2) and human breast adenocarcinoma

  摘要 含有嘧啶核 5 H-色基[4,3- d ]嘧啶（4a-c，e-h，l-r，t）和嘧啶-5-基-（2-羟基苯基）甲酮（5a，c , d , f–k , m–o , r , s , u)由脒腙(2a–u)和 3-甲酰基色酮(3)反应合成. 使用 MTT 分析方法针对人肝肝细胞癌细胞系 (HepG2) 和人乳腺腺癌细胞系 (MDA-MB-231) 测试了这些化合物。此外，还进行了分子对接计算，以比较各种新型杂环化合物对癌症蛋白质的生物活性。在这些计算中，使用的蛋白质是来自乳腺癌相关蛋白 1JNX 的 BRCT 重复区域的晶体结构、VEGFR 激酶（肝癌）蛋白的晶体结构、3WZE，以及变构 Eya2 磷酸盐抑制剂（肺癌）的晶体结构蛋白质，5ZMA，分别。经过分子对接计算、吸收、分布、代谢，
• Synthesis of novel heterocyclic compounds containing pyrimidine nucleus using the Biginelli reaction: Antiproliferative activity and docking studies
  作者：Sevtap Çağlar Yavuz、Senem Akkoç、Burçin Türkmenoğlu、Emin Sarıpınar

  DOI：10.1002/jhet.3978

  日期：2020.6

  guanyl hydrazone derivatives (3a‐n) . These compounds were tested as in vitro against two types of cancerous cell lines, namely, a human colon cancerous cell line (DLD‐1) and a human breast cancerous cell line (MDA‐MB‐231). According to the obtained results, nearly all the compounds have cytotoxic activity in the tested cell lines. Especially, the compounds 4j , 4k , and 4n had a significant effect against

  在一个反应​​步骤中，由芳香醛（1），氰基乙酸乙酯（2）和一些some衍生物（3a-n​​）的三重反应合成了嘧啶衍生物（4a-p ）。这些化合物在体外针对两种类型的癌细胞系进行了测试，分别是人结肠癌细胞系（DLD-1）和人乳腺癌细胞系（MDA-MB-231）。根据获得的结果，几乎所有化合物在测试的细胞系中均具有细胞毒活性。尤其是化合物4j，4k和4n对DLD-1具有明显的影响。此外，化合物4g，4m，和4o相比，针对MDA-MB-231的其他合成化合物，IC 50值更低。我们希望这些化合物将来可以作为抗癌药得到改进。根据拓扑异构酶I和N-乙酰转移酶1蛋白进行分子对接，从理论上检查具有最佳活性的嘧啶化合物的结合模式和位点。
• Molecular hybrids integrated with imidazole and hydrazone structural motifs: Design, synthesis, biological evaluation, and molecular docking studies
  作者：Michael Tapera、Hüseyin Kekeçmuhammed、Emin Sarıpınar、Murat Doğan、Burak Tüzün、Ümit M. Koçyiğit、Feyza Nur Çetin

  DOI：10.1016/j.molliq.2023.123242

  日期：2023.12