(S-3,4-dichlorobenzyl)isothiourea | 22297-13-8

• 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: (S-3,4-dichlorobenzyl)isothiourea
• 英文别名: S-(3,4-dichlorobenzyl)isothiourea；A22；S-(3,4-Dichlor-benzyl)-isothioharnstoff；3,4-Dichlorobenzyl Carbamimidothioate；(3,4-dichlorophenyl)methyl carbamimidothioate
• CAS: 22297-13-8
• 化学式: C₈H₈Cl₂N₂S
• mdl: MFCD21101681
• 分子量: 235.137
• InChiKey: LZTCFLDZLBOLDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  75.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S-3,4-dichlorobenzyl)isothiourea 在 sodium hydroxide 作用下， 反应 0.33h， 生成 3,4-二氯苯甲硫醇
  参考文献：
  名称：

  反式（+-）-N-甲基-2-（3-吡啶基）-2-四氢硫代吡喃碳硫酰胺1-氧化物（RP 49356）及其类似物的合成和生物活性：一类新型的钾通道开放剂。

  摘要：

  报道了反式-（+-）-N-甲基-2-（3-吡啶基）-2-四氢硫代吡喃氨基甲磺酰胺+++ e 1-氧化物（8a，RP 49356）和类似物的合成和生物活性。这些化合物构成K（+）通道开放剂的新结构类。讨论了吡啶基，硫代酰胺和硫杂环上的变化对体外K（+）通道开放反应性的影响。为了活性，优选3-吡啶基或3-喹啉基，小的N-烷基硫代酰胺官能团和氧化亚砜环，其中亚砜与硫代酰胺具有反式关系。选择的化合物在降压麻醉的大鼠中静脉内测试降压作用，其活性反映了其体外K（+）通道的开放活性。

  DOI：

  10.1021/jm00098a004
• 作为产物：
  描述：

  邻二氯苯 在 硫酸 作用下， 生成 (S-3,4-dichlorobenzyl)isothiourea
  参考文献：
  名称：

  El-Hewehi,Z., Journal fur praktische Chemie (Leipzig 1954), 1962, vol. 16, p. 201 - 206

  摘要：

  DOI：

文献信息

• THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION
  申请人：RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY

  公开号：US20190031624A1

  公开（公告）日：2019-01-31

  Disclosed herein are compounds of formula I: or a salt thereof and compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof. Also disclosed herein are methods for treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I or a pharmaceutically acceptable salt thereof, alone or in combination with a bacterial efflux pump inhibitor.

  披露于此的是公式I的化合物： 或其盐以及包含公式I化合物或其药用可接受盐的组成。还披露了用于治疗或预防动物细菌感染的方法，包括向动物单独或与细菌外排泵抑制剂联合给药公式I化合物或其药用可接受盐。
• Antibiotics targeting MreB
  申请人：Gitai Zemer

  公开号：US20060241185A1

  公开（公告）日：2006-10-26

  The identification of MreB as essential for bacterial chromosome segregation provides a new target for antibiotic action. The MreB function is useful in the development of screening assays for new antibiotics, which may use, for example, genetic mutants in MreB, tests of MreB mediated chromosome segregation, and the like. In one embodiment of the invention, the antibiotic is an isothiourea compound, which may comprise a polyhalogenated benzyl group, e.g. at the 4 position, the 2,4 position, etc. A pharmaceutical composition comprising an MreB targeted antibiotic as an active agent is administered to a patient suffering from a microbial infection, particularly bacterial infections.

  MreB的识别对于细菌染色体分离的必要性提供了新的抗生素作用靶点。MreB的功能对于开发用于新抗生素筛选的检测方法是有用的，这些方法可能包括MreB的遗传突变体、MreB介导的染色体分离等测试。在发明的一个实施例中，抗生素是一种异硫脲化合物，可能包括聚卤苯基，例如在4位、2,4位等位置。将以MreB为靶点的抗生素作为活性剂的药物组合物被用于治疗患有微生物感染，特别是细菌感染的患者。
• Structure-Activity Relationship Study of the Bacterial Actin-Like Protein MreB Inhibitors: Effects of Substitution of Benzyl Group in<i>S</i>-Benzylisothiourea
  作者：Noritaka IWAI、Takuya FUJII、Hirokatsu NAGURA、Masaaki WACHI、Tomoya KITAZUME

  DOI：10.1271/bbb.60443

  日期：2007.1.23

  We comprehensively investigated the effects of substitution of the benzyl group in S-benzylisothiourea derivatives on antibacterial activity, because we found previously that some substitutions enhanced it. A 2,4-Cl2-derivative was found to be the most effective compound, it was stronger than the original one in Gram-negative rod shaped-bacteria such as Escherichia coli and Salmonella typhimurium.

  我们全面研究了S-苄基异硫脲衍生物中苄基取代基对抗菌活性的影响，因为我们此前发现某些取代基能增强这一活性。我们发现2,4-二氯衍生物是最有效的化合物，它在革兰氏阴性杆菌如大肠杆菌和鼠伤寒沙门氏菌中的抗菌活性强于原化合物。
• Structure-Activity Relationship of<i>S</i>-Benzylisothiourea Derivatives to Induce Spherical Cells in<i>Escherichia coli</i>
  作者：Noritaka IWAI、Takuma EBATA、Hirokatsu NAGURA、Tomoya KITAZUME、Kazuo NAGAI、Masaaki WACHI

  DOI：10.1271/bbb.68.2265

  日期：2004.1

  We have previously reported that a novel S-benzylisothiourea derivative, S-(3,4-dichlorobenzyl)isothiourea, tentatively named A22, induced spherical cells in Escherichia coli. To elucidate the structural element(s) required for inducing these spherical cells, the biological activity of S-benzylisothiourea derivatives and related compounds toward E. coli cells was investigated. S-(4-Chlorobenzyl)isothiourea revealed spherical cell-inducing activity, although being slightly less potent than A22, and S-benzylisothiourea itself showed much less activity. S-Cyclohexylmethylisothiourea did not show antibacterial activity and had little effect on the cell shape. S-Heptylisothiourea showed antibacterial activity and induced elongated cells rather than spherical cells. Benzylisothiocyanate inhibited cell growth but did not induce spherical cells. S-Ethylisothiourea, benzylthiocyanate, benzylisocyanate, and N-phenylthiourea did not show any activity under the present experimental conditions. These results indicate that the S-benzylisothiourea structure was necessary and sufficient for inducing spherical cells and that 3- and/or 4-chloro-substitution of the S-benzyl group enhanced this activity.

  我们之前报道过一种新型的S-苄基异硫脲衍生物，即S-(3,4-二氯苄基)异硫脲，暂名为A22，能诱导大肠杆菌产生球状细胞。为了阐明诱导这些球状细胞所需的结构要素，我们对S-苄基异硫脲衍生物及相关化合物对大肠杆菌细胞的生物活性进行了研究。S-(4-氯苄基)异硫脲显示出诱导球状细胞的活性，尽管其效力略低于A22，而S-苄基异硫脲本身的活性则低得多。S-环己基甲基异硫脲没有显示出抗菌活性，对细胞形态影响甚微。S-庚基异硫脲表现出抗菌活性，并诱导细胞伸长而非球形化。苄基异硫氰酸酯抑制细胞生长但未诱导出球状细胞。S-乙基异硫脲、苄基硫氰酸酯、苄基异氰酸酯和N-苯基异硫脲在当前实验条件下未显示出任何活性。这些结果表明，S-苄基异硫脲结构对于诱导球状细胞既是必要的也是充分的，并且S-苄基上的3-和/或4-氯取代增强了这种活性。
• INHIBITION OF CELL PROLIFERATION
  申请人：Sebti M. Said

  公开号：US20070254318A1

  公开（公告）日：2007-11-01

  The disclosed modulators of Rb:Raf-1 interactions are potent, selective disruptors of Rb:Raf-1 binding, with IC 50 values ranging from 80 nM to 500 nM. Further, these compounds are surprisingly effective in inhibiting a wide variety of cancer cells, including osteosarcoma, epithelial lung carcinoma, non-small cell lung carcinoma, three different pancreatic cancer cell lines, two different glioblastoma cell lines, metastatic breast cancer, melanoma, and prostate cancer. Moreover, the disclosed compounds effectively disrupt angiogenesis and significantly inhibited tumors in nude mice derived from human epithelial lung carcinoma tumors. Accordingly, the disclosed compounds, pharmaceutical compositions comprising the compounds, methods of inhibiting cell proliferation, methods of treating subjects with cancer, and methods of preparing the disclosed compounds are provided.