N-(2-chloroethyl)thiomorpholine-4-carboxamide | 1257415-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: N-(2-chloroethyl)thiomorpholine-4-carboxamide
• CAS: 1257415-02-3
• 化学式: C₇H₁₃ClN₂OS
• mdl: MFCD24391176
• 分子量: 208.712
• InChiKey: KOMRSVMWQLRYEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 di-μ-sulphido-tetrakis(triphenylphosphine)-diplatinum(II) 、 N-(2-chloroethyl)thiomorpholine-4-carboxamide 以 甲醇 为溶剂， 以79%的产率得到[diplatinum(II)(μ-sulfide)(μ-SCH2CH2NHC(O)NC4H8S)(PPh3)4](PF6)
  参考文献：
  名称：

  Dinuclear platinum complexes with designer thiolate ligands from the monoalkylation of [Pt2(μ-S)2(PPh3)4]

  摘要：

  Alkylation reactions of the nucleophilic platinum(II) sulfide complex [Pt-2(mu- S)(2)(PPh3)(4)] with functionalised alkylating agents have been investigated as a versatile synthetic route to dinuclear, cationic sulfide-thiolate complexes of the type [Pt-2(mu-S)(mu-SR)(PPh3)(4)](+), extending the range of thiolate complexes that can be prepared using this methodology. A wide range of functional groups can be incorporated, using appropriate alkylating agents, and include ketone, ester, amide, hydrazone, semicarbazone, thiosemicarbazone, oxime, guanidine, urea and thiourea groups. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.07.011
• 作为产物：
  描述：

  硫代吗啉 、 氯乙基异氰酸酯 以 甲醚 为溶剂， 反应 0.08h， 生成 N-(2-chloroethyl)thiomorpholine-4-carboxamide
  参考文献：
  名称：

  吗啉和哌嗪基羧酰胺衍生物作为HCl介质中低碳钢的腐蚀抑制剂

  摘要：

  N-（2-氯乙基）吗啉-4-羧酰胺（NCMC），N-（2-氯乙基）噻吗啉-4-羧酰胺（NCTC）和N，N利用原子吸收光谱法（AAS），重量分析法和热分析法研究了-双（2-氯乙基）哌嗪-1,4-二甲酰胺（NCPD）作为低碳钢的腐蚀抑制剂。从这三种技术获得的结果是相似的，并且表明这些化合物抑制了低碳钢的腐蚀。当抑制剂浓度从10μM增加到50μM时，在30°C时，抑制效率从35.6％增至74.9％（NCMC），44.5％至82.4％（NCPD）和52.6％至90.1％（NCTC）。当温度升至50°C时，NCMC，NCPD和NCTC的最大抑制效率值（在50μM时）分别降至46.6％，58.1％和61.2％。随着温度的升高，抑制效率的降低表明金属/抑制剂相互作用的主要物理吸附机理。NCMC保护膜的形成，FTIR和XRD证实了低碳钢表面的NCPD和NCTC分子。分子的抑制强度的顺序为NCTC> NCPD>

  DOI：

  10.1016/j.molliq.2017.01.075

文献信息

• Experimental and In-Silico Investigation of Anti-Microbial Activity of 1-Chloro-2-Isocyanatoethane Derivatives of Thiomorpholine, Piperazine and Morpholine
  作者：Charles O. Nwuche、Oguejiofo T. Ujam、Akachukwu Ibezim、Ifeoma B. Ujam

  DOI：10.1371/journal.pone.0170150

  日期：——

  The Antibiogram properties of 1-chloro-2-isocyanatoethane derivatives of thiomorpholine (CTC), piperazine (CPC) and morpholine (CMC) were evaluated by the approved agar well diffusion, the minimum inhibitory concentration (MIC) and in silico techniques. A total of fourteen microbial cultures consisting of ten bacteria and four yeast strains were used in the biological study while affinity of the compounds for DNA gyrase, a validated antibacterial drug target, was investigated by docking method. Results indicate that both thiomorpholine and piperazine had zero activity against the Gram negative organisms tested. With morpholine, similar result was obtained except that cultures of Escherichia coli (ATCC 15442) and Salmonella typhi (ATCC 6539) presented with weak sensitivity (7–8 mm) as shown by the inhibition zone diameter (IZD) measurement. The Gram positive organisms were more sensitive to morpholine than the other compounds. The highest IZD values of 15–18 mm were achieved except for Streptococcus pneumoniae (ATCC 49619) in which mobility of the compound stopped after 12 mm. S. pneumoniae was resistant to both thiomorpholine and piperazine. The yeast strains were not sensitive to any of the studied compounds investigated. The MIC tests evaluated against a reference antibiotic show that while morpholine was most active at 4 μg.ml-1 against both B. cereus ATCC (14579) and B. subtilis, the least active compound was thiomorpholine which inhibited S. aureus (ATCC 25923) at 64 μg.ml-1. The three compounds demonstrated high affinity for the target protein (DNA gyrase) ranging from -4.63 to -5.64 Kcal/mol and even showed better ligand efficiencies than three known antibiotics; chlorobiocin, ciprofloxacin and tetracycline. This study identified the studied compounds as potential antibiotic leads with acceptable physicochemical properties and gave the molecular basis for the observed interactions between the compounds and the target protein which can be harnessed in structural optimization process.

  采用琼脂孔扩散法、最低抑菌浓度(MIC)和计算技术对硫代吗啉(CTC)、哌嗪(CPC)和吗啉(CMC)的1-氯-2-异氰酸基乙烷衍生物的抗菌图谱特性进行了评价。在生物学研究中使用了由10种细菌和4种酵母菌组成的14种微生物培养物,同时通过对接方法研究了这些化合物与DNA促旋酶之间的亲和性,这是一种经过验证的抗菌药物靶点。结果表明,硫代吗啉和哌嗪对测试的革兰氏阴性菌均无活性。与吗啉类似的结果表明,大肠杆菌(ATCC 15442)和伤寒沙门氏菌(ATCC 6539)的培养物表现出微弱的敏感性(7-8 mm),如抑菌圈直径(IZD)测量所示。革兰氏阳性菌对吗啉的敏感性高于其他化合物。除了肺炎链球菌(ATCC 49619)外,抑菌圈直径(IZD)的最高值为15-18 mm,该化合物的活性在12 mm处停止。肺炎链球菌对硫代吗啉和哌嗪均耐药。所研究的化合物对酵母菌均不敏感。MIC试验评估显示,吗啉对B. cereus ATCC(14579)和B. subtilis的活性最高,为4 μg/ml,而活性最低的化合物是硫代吗啉,对S. aureus(ATCC 25923)的抑制作用为64 μg/ml。这三种化合物对目标蛋白(DNA促旋酶)的亲和力较高,范围为-4.63至-5.64 kcal/mol,甚至表现出比三种已知抗生素(氯霉素、环丙沙星和四环素)更好的配体效率。该研究鉴定了所研究的化合物作为潜在的抗生素先导化合物,具有可接受的理化性质,并提供了化合物与目标蛋白之间相互作用的分子基础,可以在结构优化过程中加以利用。