N-<3-Morpholino-propyl>-N'-phenyl-thioharnstoff | 23061-68-9

• 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: N-<3-Morpholino-propyl>-N'-phenyl-thioharnstoff
• 英文别名: N-[3-(N'-phenylthioureido)propyl]morpholine；1-(3-morpholin-4-yl-propyl)-3-phenyl-thiourea；1-[3-(Morpholin-4-yl)propyl]-3-phenylthiourea；1-(3-morpholin-4-ylpropyl)-3-phenylthiourea
• CAS: 23061-68-9
• 化学式: C₁₄H₂₁N₃OS
• 分子量: 279.406
• InChiKey: RXNXLMKBZKWQHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯乙酸 、 N-<3-Morpholino-propyl>-N'-phenyl-thioharnstoff 在 sodium acetate 作用下， 生成 3-(3-吗啉基丙基)-2-(苯基亚胺)-4-噻唑烷酮
  参考文献：
  名称：

  取代的噻唑烷酮：烟酰胺腺嘌呤二核苷酸依赖性氧化的选择性抑制及其中枢神经系统活性的评估

  摘要：

  从相应的1-芳基-3-（3-N-吗啉代丙基）硫代氨基甲酸酯合成了八个2-芳基-3-（3-N-吗啉代丙基）噻唑烷-4-酮，表征并测试了它们对细胞呼吸的影响。大鼠脑匀浆的活性。所有取代的4-噻唑烷酮选择性抑制丙酮酸，柠檬酸，DL-异柠檬酸，α-酮戊二酸，苹果酸，β-羟基丁酸，L-谷氨酸和NADH的烟酰胺腺嘌呤二核苷酸（NAD）依赖性氧化，而琥珀酸的NAD依赖性氧化保持不变。所有的噻唑烷酮都具有一定程度的抗戊戊四唑诱发的惊厥的惊厥活性，这些化合物以100 mg / kg的剂量提供的保护作用范围为30％至80％。这些噻唑烷酮中的大多数具有低毒性，这是由于它们的LD-50值从300 mg / kg到大于1000 mg / kg有所反映。在本研究中，这些取代的4-噻唑烷酮所具有的抗惊厥活性与其选择性抑制大鼠脑匀浆NAD依赖性氧化的能力无关。这些噻唑烷酮显示出中枢神经系统活性降低，在某些情况下与呼吸增加有关。当以100

  DOI：

  10.1002/jps.2600640408
• 作为产物：
  描述：

  N-(3-氨丙基)吗啉 、 硫代异氰酸苯酯 以 四氢呋喃 为溶剂， 生成 N-<3-Morpholino-propyl>-N'-phenyl-thioharnstoff
  参考文献：
  名称：

  A Robust Thiourea Synthon for Crystal Engineering

  摘要：

  Crystallographic characterization of a series of bis-thiourea derivatives derived from N,N'-bis(3-aminopropyl)piperazine revealed a highly conserved intramolecular hydrogen bonding pattern, with intramolecular S(6) [or, in one case, S(8)] hydrogen bonding interactions between each heterocyclic nitrogen atom and one proton of the adjacent propylthioureido substituent. These intramolecular hydrogen-bonding interactions lend an overall spiral-like structure to the molecules, rather reminiscent of the form of a spiral galaxy. These monomeric units assemble into infinite chains via the formation of intermolecular R(2)(2)(8) cyclic thiourea dimers, with the exception of a phenyl derivative, which crystallized as a monomeric bis(dimethyl sulfoxide) solvate. The S(6) intramolecular hydrogen bond motif was maintained in the phenylthioureido derivatives of both N-(3-aminopropyl)morpholine and 3,3'-diamino-N-methyl-dipropylamine. The robustness of the "spiral galaxy" motif and its apparent ability to direct intermolecular interactions suggest its potential utility as a useful new synthon for solid-state design.

  DOI：

  10.1021/cg100589n

文献信息

• Synthetic studies on 2,4-benzothiazepin-5(1H)-one and 2,4-benzodiazepin-1-one derivatives.
  作者：HIROSHI FUJITA、YASUNOBU SATO

  DOI：10.1248/cpb.23.1764

  日期：——

  2, 4-Benzothiazepin-5 (1H)-one were usually the predominant products in reactions of o-chloromethylbenzoyl chloride with 1, 3-disubstituted thioureas ; but with methyl, benzyl or allyl substituted thioureas, 2, 4-benzodiazepin-1-ones were obtained together with 2, 4-benzothiazepin-5 (1H)-ones. These structures were elucidated from infrared, ultraviolet and nuclear magnetic resonance spectra. We also found that nature of the base and solvent as well as thiourea substituents affected the course of the reactions affording 2, 4-benzothiazepin-5 (1H)-ones or 2, 4-benzodiazepin-1-ones. Several 2, 4-benzothiazepin-5 (1H)-ones and 2, 4-benzodiazepin-1-ones possessed weak pharmacological activities, such as coronary vasodilating and local anesthetic activity.

  2, 4-苯并噻嗪-5(1H)-酮通常是邻氯甲基苯甲酰氯与1,3-双取代硫脲反应中的主要产物；但当硫脲含有甲基、苄基或烯丙基取代基时，会同时得到2, 4-苯并二氮杂䓬-1-酮与2, 4-苯并噻嗪-5(1H)-酮。这些结构通过红外、紫外和核磁共振光谱得以阐明。我们还发现，碱和溶剂的性质以及硫脲的取代基会影响反应的进程，从而生成2, 4-苯并噻嗪-5(1H)-酮或2, 4-苯并二氮杂䓬-1-酮。一些2, 4-苯并噻嗪-5(1H)-酮和2, 4-苯并二氮杂䓬-1-酮具有较弱的药理活性，如冠状动脉舒张和局部麻醉作用。
• A Robust Thiourea Synthon for Crystal Engineering
  作者：Kathryn Paisner、Lev N. Zakharov、Kenneth M. Doxsee

  DOI：10.1021/cg100589n

  日期：2010.8.4

  Crystallographic characterization of a series of bis-thiourea derivatives derived from N,N'-bis(3-aminopropyl)piperazine revealed a highly conserved intramolecular hydrogen bonding pattern, with intramolecular S(6) [or, in one case, S(8)] hydrogen bonding interactions between each heterocyclic nitrogen atom and one proton of the adjacent propylthioureido substituent. These intramolecular hydrogen-bonding interactions lend an overall spiral-like structure to the molecules, rather reminiscent of the form of a spiral galaxy. These monomeric units assemble into infinite chains via the formation of intermolecular R(2)(2)(8) cyclic thiourea dimers, with the exception of a phenyl derivative, which crystallized as a monomeric bis(dimethyl sulfoxide) solvate. The S(6) intramolecular hydrogen bond motif was maintained in the phenylthioureido derivatives of both N-(3-aminopropyl)morpholine and 3,3'-diamino-N-methyl-dipropylamine. The robustness of the "spiral galaxy" motif and its apparent ability to direct intermolecular interactions suggest its potential utility as a useful new synthon for solid-state design.
• Substituted Thiazolidones: Selective Inhibition of Nicotinamide Adenine Dinucleotide‐Dependent Oxidations and Evaluation of their CNS Activity
  作者：Sunil K. Chaudhari、Mahima Verma、Arvind K. Chaturvedi、Surendra S. Parmar

  DOI：10.1002/jps.2600640408

  日期：1975.4

  tested for their effects on the cellular respiratory activity of rat brain homogenates. All substituted 4-thiazolidones selectively inhibited nicotinamide adenine dinucleotide (NAD)-dependent oxidations of pyruvate, citrate, DL-isocitrate, alpha-ketoglutarate, malate, beta-hydroxybutyrate, L-glutamate, and NADH, while the NAD-independent oxidation of succinate remained unaltered. All thiazolidones possessed

  从相应的1-芳基-3-（3-N-吗啉代丙基）硫代氨基甲酸酯合成了八个2-芳基-3-（3-N-吗啉代丙基）噻唑烷-4-酮，表征并测试了它们对细胞呼吸的影响。大鼠脑匀浆的活性。所有取代的4-噻唑烷酮选择性抑制丙酮酸，柠檬酸，DL-异柠檬酸，α-酮戊二酸，苹果酸，β-羟基丁酸，L-谷氨酸和NADH的烟酰胺腺嘌呤二核苷酸（NAD）依赖性氧化，而琥珀酸的NAD依赖性氧化保持不变。所有的噻唑烷酮都具有一定程度的抗戊戊四唑诱发的惊厥的惊厥活性，这些化合物以100 mg / kg的剂量提供的保护作用范围为30％至80％。这些噻唑烷酮中的大多数具有低毒性，这是由于它们的LD-50值从300 mg / kg到大于1000 mg / kg有所反映。在本研究中，这些取代的4-噻唑烷酮所具有的抗惊厥活性与其选择性抑制大鼠脑匀浆NAD依赖性氧化的能力无关。这些噻唑烷酮显示出中枢神经系统活性降低，在某些情况下与呼吸增加有关。当以100