5-mercapto-1H-tetrazol-1-ylacetamide | 61197-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-mercapto-1H-tetrazol-1-ylacetamide
• 英文别名: 1-carbamoylmethyltetrazole-5-thiol；5-mercaptotetrazole-1-acetamide；2-(5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetamide；1-Carbamoylmethyltetrazol-5-thiol；2-(5-sulfanylidene-2H-tetrazol-1-yl)acetamide
• CAS: 61197-33-9
• 化学式: C₃H₅N₅OS
• 分子量: 159.172
• InChiKey: RWVPFRSKYWPNIT-UHFFFAOYSA-N

物化性质

• 熔点：
  219-220 °C (decomp)
• 沸点：
  313.8±44.0 °C(Predicted)
• 密度：
  1.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-mercapto-1H-tetrazol-1-ylacetamide 生成 1-cyanomethyl-1H-tetrazole-5-thiol
  参考文献：
  名称：

  KATNER, A. S.;BOGARD, S. J.

  摘要：

  DOI：
• 作为产物：
  描述：

  5-巯基-1H-四氮唑-1-乙酸 以74%的产率得到
  参考文献：
  名称：

  BERGES D. A.; CHAN G. W.; POLANSKY T. J.; TAGGART J. J.; DUNN G. L., J. HETEROCYCL. CHEM., 1978, 15, NO 6, 981-985

  摘要：

  DOI：

文献信息

• A new cephalosporin. SCE-963: 7-[2-(2-aminothiazol-4-yl)-acetamido]-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]-thio]methyl]ceph-3-em-4-carboxylic acid. Chemistry and structure-activity relationships.
  作者：MITSUO NUMATA、ISAO MINAMIDA、MASAYOSHI YAMAOKA、MITSURU SHIRAISHI、TOSHIO MIYAWAKI、HIROSHI AKIMOTO、KENZO NAITO、MAKOTO KIDA

  DOI：10.7164/antibiotics.31.1262

  日期：——

  The synthesis and the in vitro and in vivo antimicrobial activities of a series of 7-[2-(2-aminothiazol-4-yl)acetamido]cephalosporins (1) having varied 3-substituents, such as methyl, hydroxymethyl, acetoxymethyl, pyridiniomethyl and heterocyclicthiomethyls, are described. The derivatives having five membered heterocyclicthiomethyls exhibited strong inhibitory activities against Gram-negative organisms including some strains of Escherichia coli and Proteus morganii which are insensitive to cefazolin and cephaloridine. Pronounced activities were noted with 7-[2-(2-aminothiazol-4-yl)-acetamido]-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylic acid (1y; SCE-963).

  报道了一系列7-[2-(2-氨基噻唑-4-基)乙酰氨基]头孢菌素（1）的合成及其体外和体内的抗菌活性，这些化合物具有不同的3-取代基，如甲基、羟甲基、乙酰氧甲基、吡啶鎓甲基和杂环硫甲基等。含有五元杂环硫甲基的衍生物对包括某些对头孢唑林和头孢利定不敏感的大肠杆菌和摩根氏变形杆菌等革兰氏阴性菌表现出强烈的抑制活性。特别值得注意的是7-[2-(2-氨基噻唑-4-基)乙酰氨基]-3-[[[1-(2-二甲氨基乙基)-1H-四唑-5-基]硫]甲基]头孢-3-烯-4-羧酸（1y；SCE-963）显示了显著的活性。
• Carbapenem and penem antibiotics. II. Synthesis and antibacterial activity of 2-functionalized-methyl carbapenems related to asparenomycins.
  作者：MITSURU IMUTA、HISAO ONA、SHOICHIRO UYEO、KIYOSHI MOTOKAWA、TADASHI YOSHIDA

  DOI：10.1248/cpb.33.4361

  日期：——

  Racemic 2-acetoxymethyl and 2-(heteroaromatic) thiomethyl carbapenems having a 1-(hydroxymethyl) ethylidene or cyclic carbonate side-chain at C-6 (5, 25, 38, 40, 42, and 36b, 23b, 28b, 30b, 32b, 34b) were synthesized from the common intermediates 3a and 3b, and their antibacterial activities were determined.

  具有C-6位的1-(羟甲基)亚乙基或环状碳酸酯侧链的Racemic 2-乙酰氧甲基和2-(杂芳基)硫甲基碳青霉烯化合物（5、25、38、40、42和36b、23b、28b、30b、32b、34b）通过共同中间体3a和3b合成，并测定了它们的抗菌活性。
• Carbapenem and penem antibiotics. IV. Synthesis and antibacterial activity of (5R*,6S*)-6-((R*)-1-hydroxyethyl)-2-functionalized-methyl carbapenem and penem derivatives.
  作者：HISAO ONA、SHOICHIRO UYEO、TAKASHI FUKAO、MASAYOSHI DOI、TADASHI YOSHIDA

  DOI：10.1248/cpb.33.4382

  日期：——

  Racemic 2-acetoxymethyl and 2-(heteroaromatic) thiomethyl carbapenem and penem antibiotics having a 1-(R*)-hydroxyethyl side-chain at C-6 (6, 7, 8, and 45, 59, 47, 49, 51) were synthesized, and their antibacterial activities were determined.

  合成了R enantiomer的2-乙酰氧基甲基和2-(杂环芳香)硫甲基的碳青霉烯和青霉素抗生素，这些化合物在C-6位上具有1-(R*)-羟基乙基侧链（6, 7, 8，以及45, 59, 47, 49, 51），并测定了它们的抗菌活性。
• Carbapenem and penem antibiotics. V. Carbapenem and penem antibiotics. VI. Synthesis and antibacterial activity of 2-heteroaromatic-thiomethyl and 2-carbamoyloxymethyl 1-methylcarbapenems.
  作者：Mitsuru IMUTA、Hikaru ITANI、Hisao ONA、Yoshinori HAMADA、Shoichiro UYEO、Tadashi YOSHIDA

  DOI：10.1248/cpb.39.663

  日期：——

  chain, are described. The introduction of a methyl substituent at the C-1 position was accomplished by a newly developed procedure using crotyl halides and zinc dust. The 2-hydroxymethyl carbapenems as key intermediates allowed an easy entry into the preparation of title carbapenems.

  描述了具有6-[（（R）-1-羟乙基）侧链的1-甲基卡宾烯，2-杂芳族硫代甲基和2-氨基甲酰氧基甲基衍生物的合成和抗菌活性。通过使用巴豆基卤化物和锌粉的新开发的方法完成在C-1位上的甲基取代基的引入。以2-羟甲基碳青霉烯为主要中间体，可以轻松地制备标题碳青霉烯。
• Synthesis of 3-Substituted 2-Oxo-1,4-thiazines and Evaluation of Their Protective Effect against Endotoxin Shock in Mouse.
  作者：Hiroaki YAMAZAKI、Hidenori HARADA、Kennichi MATSUZAKI、Tetsuo WATANABE、Hirohisa SAITO

  DOI：10.1248/cpb.40.1025

  日期：——

  5-Methyl-2, 3-dioxo-2H, 4H-1, 4-thiazine (7) was obtained by the oxidation of 5-methyl-2H-1, 4-thiazin-3(4H)-one (5) with m-chloroperbenzoic acid in MeOH, followed by acid hydrolysis of the resulting 2, 2-dimethoxy-1, 4-thiazine (6). 3-Chloro-2-oxo-1, 4-thiazine (10), which was obtained from 7 by heating with phosphorous oxychloride, reacted with various nucleophiles to give 3-substituted 2-oxo-1, 4-thiazines (11a-y). Some of these 2-oxo-1, 4-thiazines, 11a-b, e, o and r-s, showed a protective effect against endotoxin shock in D-galactosamine-sensitized mice.

  5-甲基-2, 3-二氧基-2H, 4H-1, 4-噻唑啉（7）是通过用m-氯过苯甲酸在甲醇中氧化5-甲基-2H-1, 4-噻唑-3(4H)-酮（5），然后对所得的2, 2-二甲氧基-1, 4-噻唑啉（6）进行酸水解得到的。3-氯-2-氧基-1, 4-噻唑啉（10）是通过将7与氧氯化磷加热反应得到的，它与多种亲核试剂发生反应生成3-取代的2-氧基-1, 4-噻唑啉（11a-y）。其中一些2-氧基-1, 4-噻唑啉，11a-b、e、o和r-s，表现出对D-半乳糖胺敏感小鼠的内毒素休克具有保护作用。