[(6-甲基-5-氧代-2,5-二氢-1,2,4-三嗪-3-基)硫基]乙酸 | 1566-33-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: [(6-甲基-5-氧代-2,5-二氢-1,2,4-三嗪-3-基)硫基]乙酸
• 英文名称: 3-Carboxymethylmercapto-6-methyl-2,5-dihydro-1,2,4-triazinon-(5)
• 英文别名: (6-methyl-5-oxo-2(4),5-dihydro-[1,2,4]triazin-3-ylsulfanyl)-acetic acid；[(5-Hydroxy-6-methyl-1,2,4-triazin-3-yl)thio]acetic acid；2-[(6-methyl-5-oxo-4H-1,2,4-triazin-3-yl)sulfanyl]acetic acid
• CAS: 1566-33-2
• 化学式: C₆H₇N₃O₃S
• mdl: MFCD08691928
• 分子量: 201.206
• InChiKey: VIUIJRBIRXZVGL-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178 °C
• 沸点：
  370.9±44.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2933699090

反应信息

• 作为反应物：
  描述：

  [(6-甲基-5-氧代-2,5-二氢-1,2,4-三嗪-3-基)硫基]乙酸 在 乙酸酐 作用下， 生成 2-methyl-thiazolo[3,2-b][1,2,4]triazine-3,7-dione
  参考文献：
  名称：

  Shafiee,A.; Lalezari,I., Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 1011 - 1014

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium monochloroacetic acid 、 6-氮杂-2-硫代胸腺嘧啶 在 乙醇 作用下， 生成 [(6-甲基-5-氧代-2,5-二氢-1,2,4-三嗪-3-基)硫基]乙酸
  参考文献：
  名称：

  Carboxymethylmercapto compounds as stabilizers for photographic emulsions

  摘要：

  以下杂环巯基化合物在水溶液中与氯乙酸钠加热，生成相应的羧甲基巯基衍生物；1-苯基-2-咪唑硫酮，2-巯基嘧啶及其4,6-二氨基-, 4,5,6-三氨基-, 4-氨基-6-羟基或4-羟基-6-甲基衍生物，2-巯基苯并噁唑，2-巯基苯并噻唑，3-苯基（或氨基）-4-氨基-5-巯基-1,2,4-三唑，3-巯基-5-羟基（或苯基）6-甲基-1,2,4-三嗪和2-巯基-咪唑啉及其4-甲基衍生物。通过将氯乙酸加入水溶性氢氧化钠中的2-巯基-4,6-二氨基-S-三嗪溶液制备2-羧甲基巯基-4,6-二氨基-S-三嗪。通过在水溶性氢氧化钠中搅拌溴辛酸和4,6-二氨基-2-巯基-S-三嗪的溶液制备2-(1-羧基辛基巯基)-4,6-二氨基-S-三嗪。通过在水中将2-巯基咪唑啉和氯乙酸反应制备2-羧甲基巯基-咪唑啉酸氯乙酸酯。参考规格235,211和634,951。

  公开号：

  US02819965A1

文献信息

• Small molecules for inhibiting male fertility
  申请人：The University of North Carolina at Chapel Hill

  公开号：US10472334B2

  公开（公告）日：2019-11-12

  Compounds suitable for use in providing male contraception, an assay method for identifying such compounds, and methods of providing contraception using the compounds, are provided. In one embodiment, the compounds described herein mimic the binding of anti-EPPIN antibodies to EPPIN, and thus inhibit the forward motility of sperm in humans and other primates. In another embodiment, the compounds described herein inhibit or enhance EPPIN-semenogelin binding, and inhibit forward motility of sperm. The assays described herein identify compounds which inhibit sperm motility, and can be carried out in a high throughput manner, using labeled recombinant EPPIN and semenogelin. The compounds can be used in oral or transdermal compositions to temporarily and reversibly inhibit male fertility. They can also be used in addition to, or in place of, spermicides in spermicidal compositions, such as those used in conjunction with condoms, diaphragms, and spermicidal jellies.

  本研究提供了适用于男性避孕的化合物、鉴定此类化合物的检测方法以及使用这些化合物进行避孕的方法。在一个实施方案中，本文所述化合物模拟抗 EPPIN 抗体与 EPPIN 的结合，从而抑制人类和其他灵长类动物精子的前向运动。在另一个实施方案中，本文所述化合物可抑制或增强 EPPIN 与脑膜鞘氨醇的结合，从而抑制精子的前向运动。本文所述的检测方法可鉴定出抑制精子活力的化合物，并可使用标记的重组 EPPIN 和精蛋白硒以高通量的方式进行检测。这些化合物可用于口服或透皮组合物，以暂时、可逆地抑制男性生育能力。它们还可以在杀精组合物中作为杀精剂的补充或替代物使用，例如与避孕套、避孕膜和杀精果冻一起使用的组合物。
• Gut; Prystas, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 2986,2988
  作者：Gut、Prystas

  DOI：——

  日期：——
• SMALL MOLECULES FOR INHIBITING MALE FERTILITY
  申请人：The University of North Carolina at Chapel Hill

  公开号：US20170057934A1

  公开（公告）日：2017-03-02

  Compounds suitable for use in providing male contraception, an assay method for identifying such compounds, and methods of providing contraception using the compounds, are provided. In one embodiment, the compounds described herein mimic the binding of anti-EPPIN antibodies to EPPIN, and thus inhibit the forward motility of sperm in humans and other primates. In another embodiment, the compounds described herein inhibit or enhance EPPIN-semenogelin binding, and inhibit forward motility of sperm. The assays described herein identify compounds which inhibit sperm motility, and can be carried out in a high throughput manner, using labeled recombinant EPPIN and semenogelin. The compounds can be used in oral or transdermal compositions to temporarily and reversibly inhibit male fertility. They can also be used in addition to, or in place of, spermicides in spermicidal compositions, such as those used in conjunction with condoms, diaphragms, and spermicidal jellies.