4-hydroxybenzaldehyde semicarbazone | 120445-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxybenzaldehyde semicarbazone
• 英文别名: (E)-2-(4-hydroxybenzylidene)hydrazine-1-carboxamide；p-hydroxybenzaldehyde semicarbazone；4-OHBS；4-Hydroxybenzaldehyde semicarbazone；[(E)-(4-hydroxyphenyl)methylideneamino]urea
• CAS: 120445-50-3
• 化学式: C₈H₉N₃O₂
• 分子量: 179.178
• InChiKey: VDPCABXJOAHHDE-BJMVGYQFSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 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：
  87.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxybenzaldehyde semicarbazone 以68%的产率得到
  参考文献：
  名称：

  SOLIMAN F. S. G.; SHAFIK R. M.; DARWISH M., PHARMAZIE, 1979, 34, NO 3, 198-199

  摘要：

  DOI：
• 作为产物：
  描述：

  盐酸氨基脲 、 对羟基苯甲醛 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以73%的产率得到4-hydroxybenzaldehyde semicarbazone
  参考文献：
  名称：

  New trypanocidal hybrid compounds from the association of hydrazone moieties and benzofuroxan heterocycle

  摘要：

  Hybrid compounds containing hydrazones and benzofuroxan pharmacophores were designed as potential Trypanosoma cruzi-enzyme inhibitors. The majority of the designed compounds was successfully synthesized and biologically evaluated displaying remarkable in vitro activity against different strains of T. cruzi. Unspecific cytotoxicity was evaluated using mouse macrophages, displaying isothiosemicarbazone 10 and thiosemicarbazone 12 selectivity indexes (macrophage/parasite) of 21 and 27, respectively. In addition, the mode of anti-trypanosomal action of the derivatives was investigated. Some of these derivatives were moderate inhibitors of cysteinyl active site enzymes of T. cruzi, cruzipain and trypanothione reductase. ESR experiments using T. cruzi microsomal fraction suggest that the main mechanism of action of the trypanocidal effects is the production of oxidative stress into the parasite. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.038

文献信息

• Synthesis of aryl-hydrazones via ultrasound irradiation in aqueous medium
  作者：Ana Cristina Lima Leite、Diogo Rodrigo de M. Moreira、Lucas Cunha Duarte Coelho、Frederico Duarte de Menezes、Dalci José Brondani

  DOI：10.1016/j.tetlet.2007.12.103

  日期：2008.2

  The synthesis of aryl-hydrazones from aromatic aldehydes/ketones and hydrazides (semicarbazide, thiosemicarbazide and aminoguanidine) is described using aqueous medium (acid conditions) under ultrasound irradiation with short reaction times (20–30 min), the reactions occurring at room temperature and giving rise to good to excellent yields of the products, along with the diastereoselectivities. The

  描述了使用水性介质（酸性条件）在短时间（20-30分钟）超声辐照下，由芳族醛/酮和酰肼（氨基脲，氨基脲和氨基胍）合成芳基hydr的反应，该反应发生在室温和与非对映选择性一起产生了很好的产品收率。程序也简单干净。
• Design, synthesis and biological evaluation of N-oxide derivatives with potent in vivo antileishmanial activity
  作者：Leandro da Costa Clementino、Guilherme Felipe Santos Fernandes、Igor Muccilo Prokopczyk、Wilquer Castro Laurindo、Danyelle Toyama、Bruno Pereira Motta、Amanda Martins Baviera、Flávio Henrique-Silva、Jean Leandro dos Santos、Marcia A. S. Graminha

  DOI：10.1371/journal.pone.0259008

  日期：——

  Leishmaniasis is a neglected disease that affects 12 million people living mainly in developing countries. Herein, 24 new N-oxide-containing compounds were synthesized followed by in vitro and in vivo evaluation of their antileishmanial activity. Compound 4f, a furoxan derivative, was particularly remarkable in this regard, with EC₅₀ value of 3.6 μM against L. infantum amastigote forms and CC₅₀ value superior to 500 μM against murine peritoneal macrophages. In vitro studies suggested that 4f may act by a dual effect, by releasing nitric oxide after biotransformation and by inhibiting cysteine protease CPB (IC₅₀: 4.5 μM). In vivo studies using an acute model of infection showed that compound 4f at 7.7 mg/Kg reduced ~90% of parasite burden in the liver and spleen of L. infantum-infected BALB/c mice. Altogether, these outcomes highlight furoxan 4f as a promising compound for further evaluation as an antileishmanial agent.

  利什曼病是一种影响主要发展中国家居民的1200万人的被忽视的疾病。在这项研究中，合成了24种新的含氧化物的化合物，随后评估了它们的抗利什曼病活性。其中，一种呋喃氧化物衍生物4f在这方面表现尤为出色，对婴儿利什曼体形式的EC50值为3.6μM，对小鼠腹膜巨噬细胞的CC50值超过500μM。体外研究表明，4f可能通过双重作用发挥作用，经生物转化后释放一氧化氮，并抑制半胱氨酸蛋白酶CPB（IC50：4.5μM）。使用急性感染模型的体内研究表明，7.7毫克/千克的4f化合物可使感染婴儿利什曼体的BALB/c小鼠肝脏和脾脏中的寄生虫负担减少约90%。总的来说，这些结果突出了呋喃氧化物4f作为一种有前途的化合物，值得进一步评估其作为抗利什曼病药物的潜力。
• Structure-Based Discovery of Thiosemicarbazone Metalloproteinase Inhibitors for Hemorrhage Treatment in Snakebites
  作者：Francis B. Ferreira、Thiago M. Pereira、Dayane L. N. Souza、Daiana S. Lopes、Vitor Freitas、Veridiana M. R. Ávila、Arthur E. Kümmerle、Carlos Mauricio R. Sant’Anna

  DOI：10.1021/acsmedchemlett.7b00186

  日期：2017.11.9

  The venoms of snakes are composed by many toxins, which are responsible for various toxic effects including intense pain, bleeding disorders, and local tissue damage caused by hemorrhage and necrosis. The snake venom metalloproteinases (SVMPs) are proteolytic zinc-dependent enzymes acting in different hemostatic mechanisms. In this work, a structure-based molecular modeling strategy was used for the rational design, by means of a homology 3D model of an SVMP isolated from Bothrops pauloensis venom (BpMP-I), followed by synthesis and in vitro evaluation of new thiosemicarbazones as the first inhibitors of the B. pauloensis SVMP. Besides being effective for the SVMP inhibition, two molecules were shown to be effective also in vivo, inhibiting hemorrhage caused by the B. pauloensis whole venom. Docking studies on metalloproteinases from other snake species suggest that the thiosemicarbazones activity is not confined to BpMP-I, but seems to be a common feature of metzincins.
• MOHAMED M. M.; EL HASHASH M. A.; EL KADY M. Y.; HASSAN M. A., REV. ROUM. CHIM., 1980, 25, NO 2, 237-244
  作者：MOHAMED M. M.、 EL HASHASH M. A.、 EL KADY M. Y.、 HASSAN M. A.

  DOI：——

  日期：——
• CANO, A. C.;DELGADO, F.;CORDOBA, A. A.;MARQUEZ, C.;ALVAREZ, C., SYNTH. COMMUN., 18,(1988) N 16-17, C. 2051-2053
  作者：CANO, A. C.、DELGADO, F.、CORDOBA, A. A.、MARQUEZ, C.、ALVAREZ, C.

  DOI：——

  日期：——