N-<(Methylthio)thiocarbonyl>β-alanine | 61606-28-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-<(Methylthio)thiocarbonyl>β-alanine
• 英文别名: methyl 2-carboxyethyldithiocarbamate；N-[(Methylthio)thiocarbonyl]β-alanine；3-(methylsulfanylcarbothioylamino)propanoic acid
• CAS: 61606-28-8
• 化学式: C₅H₉NO₂S₂
• 分子量: 179.264
• InChiKey: PBBKFUOGKZPENI-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  332.3±44.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(Methylthio)thiocarbonyl>β-alanine 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-Oxo-6-(4-oxo-2-thioxo-3-ethylthiazolidin-5-ylidene)-8-phenyl-1,2,3,4-tetrahydro-6H-thiazolo<3,4-a>pyrimidine
  参考文献：
  名称：

  带有噻唑环的稠合杂环。6.制备咪唑并[1,2-c]噻唑鎓和噻唑并[3,4-a]嘧啶鎓盐的新方法

  摘要：

  DOI：

  10.1007/bf00506101
• 作为产物：
  描述：

  β-丙氨酸 、 碘甲烷 在 二硫化碳 、 氢氧化钾 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 生成 N-<(Methylthio)thiocarbonyl>β-alanine
  参考文献：
  名称：

  7-Acylamino-3-(substituted tetrazolyl thiomethyl) cephalosporins

  摘要：

  这项发明的化合物是头孢菌素，其在7-位置具有各种酰基取代基，并且在头孢菌素核的3-位置具有取代的四唑基硫甲基基团，并提供了其制备的中间体。7-酰化化合物具有抗菌活性。

  公开号：

  US04220644A1

文献信息

• 4,5-Dihydro-5-thioxo-]<i>H</i>-tetrazoie-l-alkanoic and alkanesulfonic acids and their amide derivatives
  作者：David A. Berges、George W. Chan、Theodore J. Polansky、John J. Taggart、George L. Dunn

  DOI：10.1002/jhet.5570150615

  日期：1978.9

  Homologous 4,5-dihydro-5-thioxo-1H-tetrazole-l-alkanoic and alkanesulfonic acids were prepared by reaction of sodium azide with methyl (carboxyalkyl)- and (sulfoalkyl) carbamodithioates, respectively. 4,5-Dihydro-5-thioxo-1H-tetrazole-i-alkanamides were derived from the corresponding alkanoic acids by aminolysis of their acid chlorides or imidazolides. Analogous alkane-sulfonamides were synthesized

  通过叠氮化钠分别与（羧烷基）-和（磺烷基）氨基甲酸二硫代甲烷酯反应，制备同源的4，5-二氢-5-噻吩-1- H-四唑-1-链烷酸和链烷磺酸。通过相应的链烷酸的酰氯或咪唑化物的氨解反应，可以从相应的链烷酸衍生得到4,5-二氢-5-噻吩-1 H-四唑-1-烷基酰胺。通过[[[（（（1,1-二甲基乙基）氨基]磺酰基]-烷基氨基甲酸二硫代甲基酯与叠氮化钠的反应，然后用三氟乙酸除去1,1-二甲基乙基，合成了类似的烷烃-磺酰胺。
• 7-Alpha-oxyiminoacylcephalosporins
  申请人：SmithKline Corporation

  公开号：US04278670A1

  公开（公告）日：1981-07-14

  New semisynthetic cephalosporins having antibacterial activity are described. The structures of the new compounds are characterized by having an .alpha.-oxyimino group in the 7-acetamidomoiety plus a carboxyalkyltetrazolylthiomethyl group at position 3.

  本文描述了具有抗菌活性的新型半合成头孢菌素。新化合物的结构特点是7-乙酰胺基上有一个α-氧肟基团，同时在3号位上有一个羧基烷基四唑硫甲基基团。
• 7-Acyl-3-(substituted tetrazolyl thiomethyl)cephalosporins
  申请人：SmithKline Corporation

  公开号：US04286089A1

  公开（公告）日：1981-08-25

  The compounds of this invention are cephalosporins having various acyl substituents at the 7-position and a substituted tetrazolyl thiomethyl group at the 3-position of the cephem nucleus and intermediates for the preparation thereof. The 7-acylated compounds have antibacterial activity.

  这项发明的化合物是头孢菌素，其在7位具有不同的酰基取代基和在头孢环上的3位有取代的四唑硫甲基基团，同时也提供了其制备的中间体。7-酰化的化合物具有抗菌活性。
• Synthesis and Biological Activity of Aminoguanidine and Diaminoguanidine Analogues of the Antidiabetic/Antiobesity Agent 3-Guanidinopropionic Acid
  作者：Valerie A. Vaillancourt、Scott D. Larsen、Steven P. Tanis、Jeffery E. Burr、Mark A. Connell、Michele M. Cudahy、Bruce R. Evans、Peter V. Fisher、Paul D. May、Martin D. Meglasson、Deborah D. Robinson、F. Craig Stevens、John A. Tucker、Thomas J. Vidmar、Jen H. Yu

  DOI：10.1021/jm000094n

  日期：2001.4.1

  3-Guanidinopropionic acid (1) has been demonstrated both to improve insulin sensitivity and to promote weight loss selectively from adipose tissue in animal models of non-insulin-dependent diabetes mellitus (NIDDM). However, 1 has also been shown to be a substrate for both the creatine transporter and creatine kinase, leading to marked accumulation in muscle tissue as the corresponding N-phosphate. The corresponding aminoguanidine analogue 2 was recently discovered to retain the antidiabetic activity of 1 while being markedly less susceptible to creatine-like metabolism, suggesting that it should have less potential to accumulate in muscle. Further structural modification of 2 was undertaken to investigate whether the antidiabetic potency could be augmented while maintaining resistance to creatine-like metabolism. Modifications such as a-alkylation, homologation, and bioisosteric replacement of the aminoguanidine all were detrimental to antidiabetic activity. However, the simple regioisomeric aminoguanidinoacetic acid 9 and diaminoguanidinoacetic acid-analogue 7 were found to be equipotent to 2, leading eventually to the discovery of the significantly more potent diaminoguanidinoacetic acid regioisomers 52 and 53. Further attempts to modify the more active template represented by 52 led only to reductions in; antidiabetic activity. Each of the new active analogues displayed the same resistance to creatine-like metabolism as 2. Further testing of 7, 9, and 53 in obese diabetic ob;lob mice confirmed that weight loss is induced selectively from adipose tissue, similar to the lead 1. Administration of 53 to insulin-resistant rhesus monkeys led to reductions in both fasting and post-prandial plasma glucose levels with concomitant reductions in plasma insulin levels, suggesting that the compound improved the action of endogenous insulin. Compounds 7 and 53 were selected for further preclinical development.
• BERGES, D. A.
  作者：BERGES, D. A.

  DOI：——

  日期：——