<2-(tritylamino)thiazol-4-yl>acetyl chloride | 115385-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: <2-(tritylamino)thiazol-4-yl>acetyl chloride
• 英文别名: 2-Triphenylmethylaminothiazol-4-yl Acetyl Chloride；{2-[(Triphenylmethyl)amino]-1,3-thiazol-4-yl}acetyl chloride；2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl chloride
• CAS: 115385-02-9
• 化学式: C₂₄H₁₉ClN₂OS
• 分子量: 418.947
• InChiKey: GGIJWBBVZOLQRS-UHFFFAOYSA-N

物化性质

• 沸点：
  588.1±60.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <2-(tritylamino)thiazol-4-yl>acetyl chloride 在 甲酸 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 头孢地尼杂质B
  参考文献：
  名称：

  Oral absorption of cephalosporin antibiotics. 1. Synthesis, biological properties and oral bioavailability of 7-arylacetamido-3-chloro cephalosporins in animals

  摘要：

  A number of 7-(arylacetamido)-3-substituted cephalosporins were prepared and tested in animals for oral absorbability. Bioavailability in mice, rats, dogs, and monkeys was determined after oral or parenteral administration. Oral bioavailability of five compounds selected for more intensive study was generally higher than that of penicillin V in all species tested. The results of ED50 testing against experimental infections in mice generally supported the bioavailability studies. Antibiotic activities were evaluated against Gram-positive and Gram-negative organisms with some derivatives expressing in vitro activity similar to cefaclor. The plasma half-life in rats was relatively short and the plasma curves were strongly influenced by probenecid, indicating rapid renal secretion. Some 7-(arylacetamido)-3-chloro cephalosporins are orally absorbed in animals to a greater extent than penicillin V, and antibacterial agent of proven clinical utility.

  DOI：

  10.1021/jm00118a022
• 作为产物：
  描述：

  <2-(tritylamino)thiazol-4-yl>acetic acid 在 草酰氯 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 <2-(tritylamino)thiazol-4-yl>acetyl chloride
  参考文献：
  名称：

  Oral absorption of cephalosporin antibiotics. 1. Synthesis, biological properties and oral bioavailability of 7-arylacetamido-3-chloro cephalosporins in animals

  摘要：

  A number of 7-(arylacetamido)-3-substituted cephalosporins were prepared and tested in animals for oral absorbability. Bioavailability in mice, rats, dogs, and monkeys was determined after oral or parenteral administration. Oral bioavailability of five compounds selected for more intensive study was generally higher than that of penicillin V in all species tested. The results of ED50 testing against experimental infections in mice generally supported the bioavailability studies. Antibiotic activities were evaluated against Gram-positive and Gram-negative organisms with some derivatives expressing in vitro activity similar to cefaclor. The plasma half-life in rats was relatively short and the plasma curves were strongly influenced by probenecid, indicating rapid renal secretion. Some 7-(arylacetamido)-3-chloro cephalosporins are orally absorbed in animals to a greater extent than penicillin V, and antibacterial agent of proven clinical utility.

  DOI：

  10.1021/jm00118a022

文献信息

• Oral absorption of cephalosporin antibiotics. 3. Synthesis and biological properties of 7.alpha.-methoxy-7.beta.-arylacetamido-3-chloro-3-cephem-4-carboxylic acids
  作者：Janice Pfeil-Doyle、Stjepan Kukolja

  DOI：10.1021/jm00118a024

  日期：1988.10

  A series of 7 alpha-methoxy-7 beta-amido-3-chloro-3-cephem-4-carboxylic acids was prepared and evaluated for biological activity. When compared with the parent 7-non-methoxy analogues, these new 7 alpha-methoxy-3-chloro cephalosporins displayed diminished antimicrobial activity.

  制备了一系列的7种α-甲氧基-7β-氨基-3-氯-3-cephem-4-羧酸，并对其生物学活性进行了评估。当与母体7-非甲氧基类似物相比时，这些新的7α-甲氧基-3-氯头孢菌素显示出降低的抗菌活性。
• Antibiotic derivatives of
  申请人：Eli Lilly and Company

  公开号：US04683227A1

  公开（公告）日：1987-07-28

  7.beta.-Heterocyclicacetylamino-(and 7.beta.-heterocyclicthioacetamido)-3-chloro-3-cephem-4-carboxylic acids and pharmaceutically acceptable salts thereof, e.g., 7.beta.-[2-(2-aminothiazol-4-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acid and salts thereof, exhibit surprising peroral bioavailability and are useful in a method for treating infections in man and animals and in formulations for oral administration.

  7-beta-杂环乙酰胺基-(和7-beta-杂环硫代乙酰胺基)-3-氯-3-头孢-4-羧酸及其药用盐，例如7-beta-[2-(2-氨基噻唑-4-基)乙酰胺基]-3-氯-3-头孢-4-羧酸及其盐，表现出惊人的口服生物利用度，在治疗人和动物感染的方法和口服制剂中有用。
• Cephalosporins, their preparation and formulations
  申请人：ELI LILLY AND COMPANY

  公开号：EP0211526A2

  公开（公告）日：1987-02-25

  7p-Heterocyclicacetylamino-(and 7β-heterocyclic- thioacetamido)-3-chloro-3-cephem-4-carboxylic acids or pharmaceutically acceptable salts thereof (e.g., 7β-[2-(2-aminothiazol-4-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acid and salts thereof) exhibit surprising peroral bioavailability and are useful for treating infections in a warm-blooded animal. The have the formula in which R is a 5-membered nitrogen-containing heterocyclic ring of the formulae or Y is S or a bond; in which in the above formulae Z is O, S, or N and R' is hydrogen, hydroxy, halo, amino, C1-C4 alkanoylamino, C1-C4 alkylamino, di-(C1-C4 alkyllamino, C1-C4 alkylsulfonylamino, C1-C4 alkanoyloxy, C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 alkyl, phenyl, or trihalomethyl; R1 is hydrogen, methoxy, or formamido; or a pharmaceutically acceptable salt thereof.

  7p-杂环乙酰氨基-（和 7β-杂环-硫代乙酰氨基）-3-氯-3-头孢-4-羧酸或其药学上可接受的盐（例如，7β-[2-（2-氨基噻唑-4-基）乙酰氨基]-3-氯-3-头孢-4-羧酸及其盐）具有惊人的口服生物利用度，可用于治疗温血动物的感染。它们的化学式为 其中 R 是式中的 5 元含氮杂环 或 Y 是 S 或键； 其中上式中 Z 是 O、S 或 N，R'是氢、羟基、卤代、氨基、C1-C4 烷酰氨基、C1-C4 烷基氨基、二（C1-C4 烷基氨基、C1-C4 烷基磺酰氨基、C1-C4 烷酰氧基、C1-C4 烷氧基、C1-C4 烷基磺酰氧基、C1-C4 烷基、苯基或三卤甲基； R1 是氢、甲氧基或甲酰胺基；或其药学上可接受的盐。
• Structure-activity relationship within a series of pyrazolidinone antibacterial agents. 2. Effect of side-chain modification on in vitro activity and pharmacokinetic parameters
  作者：Robert J. Ternansky、Susan E. Draheim、Andrew J. Pike、Fred T. Counter、Judy A. Eudaly、Jeffrey S. Kasher

  DOI：10.1021/jm00074a002

  日期：1993.10

  The structure-activity relationship among a series of novel pyrazolidinone antibacterial agents is described. Specifically, the effect of modification of the side chain attached to the nitrogen at C-7 was explored in an attempt to improve the potency and spectrum of activity. This approach was successful in identifying several compounds having good in vitro profiles. These top candidates were then evaluated for their activity in vivo, and their pharmacokinetic behavior in various animal models was explored. This information proved critical for the identification of candidates for clinical evaluation.
• KUKOLJA, STJEPAN;WRIGHT, WALTER E.;QUAY, JOHN F.;PFEIL-DOYLE, JANICE;DRAH+
  作者：KUKOLJA, STJEPAN、WRIGHT, WALTER E.、QUAY, JOHN F.、PFEIL-DOYLE, JANICE、DRAH+

  DOI：——

  日期：——