2-(2-tritylamino-4-thiazolyl)-2-(2-propenyl)-oxyimino-acetic acid | 64485-96-7

• 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-(2-tritylamino-4-thiazolyl)-2-(2-propenyl)-oxyimino-acetic acid
• 英文别名: (Z)-2-Allyloxyimino-2-(2-tritylaminothiazol-4-yl)-acetic acid；(Z)-allyloxyimino-(2-tritylamino-thiazol-4-yl)-acetic acid；(Z)-2-(2-propen-1-oxyimino)-2-[2-(triphenylmethyl)aminothiazol-4-yl]acetic acid；2-(2-tritylamino-4-thiazolyl)-2-(2-propenyloxyimino)-acetic acid；(Z)-2-allyloxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid；(2Z)-2-prop-2-enoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid
• CAS: 64485-96-7
• 化学式: C₂₇H₂₃N₃O₃S
• 分子量: 469.564
• InChiKey: HHMMCKKDCSBYLE-KRUMMXJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-tritylamino-4-thiazolyl)-2-(2-propenyl)-oxyimino-acetic acid 在 N-甲基吗啉 、 三乙基硅烷 、 三氟乙酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 3.42h， 生成 (S)-6-[2-[(Z)-Allyloxyimino]-2-(2-amino-thiazol-4-yl)-acetylamino]-2-methanesulfonyl-7-oxo-6,7-dihydro-3H,5H-pyrazolo[1,2-a]pyrazole-1-carboxylic acid allyl ester
  参考文献：
  名称：

  Structure-activity relationship within a series of pyrazolidinone antibacterial agents. 2. Effect of side-chain modification on in vitro activity and pharmacokinetic parameters

  摘要：

  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.

  DOI：

  10.1021/jm00074a002
• 作为产物：
  描述：

  ethyl (Z)-2-hydroxyimino-2-(2-triphenylmethylaminothiazol-4-yl)acetate 在 potassium carbonate 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-tritylamino-4-thiazolyl)-2-(2-propenyl)-oxyimino-acetic acid
  参考文献：
  名称：

  对在肟残基上带有多个取代基的单bactams革兰氏阴性细菌的耐药性进行合成和抗菌评估。

  摘要：

  根据氨曲南（AZN）及其目标PBP3的结构特征，制备了一系列在肟残基上带有各种取代基的新型单bactam衍生物，并评估了它们对敏感和耐药革兰氏阴性细菌的抗菌活性。其中，化合物8p和8r对大多数测试的革兰氏阴性菌株表现出中等效力，MIC值为0.125-32μg/ mL，与AZN相当。同时，以1:16的比例将8p和8r与avibactam作为β-内酰胺酶抑制剂的组合显示出对产生ESBLs和NDM-1的肺炎克雷伯菌的有希望的协同作用，并且MIC值显着降低分别为8倍和> 256倍。此外，它们在体外和体内均显示出优异的安全性。

  DOI：

  10.1016/j.bioorg.2019.103487

文献信息

• 3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives
  申请人：Roussel Uclaf

  公开号：US04152432A1

  公开（公告）日：1979-05-01

  Compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and groups easily removable by acid hydrolysis or hydrogenolysis, R' is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, alkenyl and alkynyl of 2 to 4 carbon atoms and groups easily removable by acid hydrolysis or hydrogenolysis, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal or magnesium and an organic amine base with the proviso that when R' is a group easily removable by acid hydrolysis or hydrogenolysis, R is also and when R' is hydrogen, R also is hydrogen and the wavy line means the OR' group may be in either one of the two possible syn or anti positions having antibiotic activity and process for their preparation.

  式为##STR1##的化合物，其中R从氢和易于酸水解或氢解的基团中选择，R'从氢、1至4个碳原子的烷基、2至4个碳原子的烯基和炔基以及易于酸水解或氢解的基团中选择，A从氢、碱金属和碱土金属或镁的当量物以及有抗生素活性的有机胺基中选择，但当R'是易于酸水解或氢解的基团时，R也是如此；当R'是氢时，R也是氢；波浪线表示OR'基团可以处于两种可能的同构或反构位置之一，具有抗生素活性和其制备方法。
• Cephalosporins
  申请人：Bristol-Myers Company

  公开号：US04406899A1

  公开（公告）日：1983-09-27

  Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or a conventional amino-protecting group, and R.sup.2 is a straight or branched chain alkyl group containing from 1 to 4 carbon atoms, allyl, 2-butenyl or 3-butenyl, and nontoxic pharmaceutically acceptable salts and solvates thereof, as well as processes for their preparation, are disclosed. The compounds in which R.sup.1 is hydrogen are potent antibacterial agents.

  该公式化合物的化合物中，其中R.sup.1是氢或传统的氨基保护基团，而R.sup.2是含有1至4个碳原子的直链或支链烷基基团，烯丙基，2-丁烯基或3-丁烯基，以及其无毒的药用可接受盐和溶剂，以及它们的制备方法。其中R.sup.1为氢时的化合物是有效的抗菌剂。
• Cephalosporines a chaines amino-2 thiazolyl-4 acetyles
  作者：R. Bucourt、R. Heymes、A. Lutz、L. Pénasse、J. Perronnet

  DOI：10.1016/0040-4020(78)89034-6

  日期：1978.1

  The syntheses of 2-(2-amino-4-thiazolyl) 2-(hydroxy or alkoxy)-imino acetic acid derivatives, with the anti (E) and syn (Z) configurations, are described. By means of these compounds, the acylation of the amino-group of 7β-amino cephalosporanic acid (7-ACA) has been achieved. The two resulting series of cephalosporin derivatives-anti and syn-are markedly different with respect to their antibiotic activity

  描述了具有反（E）和顺（Z）构型的2-（2-氨基-4-噻唑基）2-（羟基或烷氧基）-亚氨基乙酸衍生物的合成。通过这些化合物，已经实现了7β-氨基头孢烷酸（7-ACA）的氨基的酰化。这两个由此带来的一系列的头孢derivatives-防和顺式相对于它们的抗菌活性-are明显不同。一些合成化合物具有迄今为止所观察到的最高的抗菌活性。
• Cephalosporin derivatives
  申请人：Bristol-Myers Company

  公开号：US04486586A1

  公开（公告）日：1984-12-04

  7-(Z)-2-(2-Aminothiazol-4-yl)-2-[(substituted)oxyimino]acetamido}-3-[3-(qu aternary ammonio)-1-propen-1-yl]-3-cephem-4-carboxylates and salts, esters and solvates thereof, having potent antibacterial activity, are provided. Processes for their preparation and intermediates in their preparation also are disclosed.

  提供具有强效抗菌活性的7-(Z)-2-(2-氨基噻唑-4-基)-2-[(取代)氧肟基]乙酰氨基}-3-[3-(季铵)-1-丙烯-1-基]-3-头孢烯-4-羧酸盐、酯和溶剂化物。还公开了制备它们的方法和制备中间体。
• Chemical compounds
  申请人：Bristol-Myers Company

  公开号：US04507487A1

  公开（公告）日：1985-03-26

  Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or a conventional amino-protecting group, R.sup.2 is a straight or branched chain alkyl group containing from 1 to 4 carbon atoms, allyl, 2-butenyl, 3-butenyl, propargyl, 2-butynyl, 3-butynyl, cycloalkyl containing from 3 to 6 carbon atoms or a group of the formula ##STR2## in which R.sup.3 and R.sup.4 each are independently hydrogen, methyl or ethyl, or R.sup.3 and R.sup.4, taken together with the carbon atom to which they are attached, may be a cycloalkylidene ring containing from 3 to 6 carbon atoms or a substituted cyclobutylidene ring of the formula ##STR3## wherein X is halogen, hydroxy or (lower)alkoxy, and R.sup.5 and R.sup.6 each are independently hydrogen, halogen, amino, carbamoyl, acylamino, acyloxy, (lower)alkyl, (lower)alkenyl, (lower)alkoxy, (lower)alkylamino or (lower)alkylthio, in which each (lower)alkyl, (lower)alkoxy, (lower)alkylamino or (lower)alkylthio group may contain 1 or 2 substituents selected from amino, carboxy, halogen and nontoxic pharmaceutically acceptable acid addition salts, physiologically hydrolyzable esters and solvates thereof, as well as processes for their preparation, are disclosed. The compounds in which R.sup.1 is hydrogen are potent antibacterial agents.

  本发明涉及公式##STR1##的化合物，其中R.sup.1为氢或传统的氨基保护基，R.sup.2为直链或支链烷基，含有1至4个碳原子，烯丙基，2-丁烯基，3-丁烯基，丙炔基，2-丁炔基，3-丁炔基，含有3至6个碳原子的环烷基或公式##STR2##的基团，其中R.sup.3和R.sup.4各自独立地为氢，甲基或乙基，或R.sup.3和R.sup.4与它们所连接的碳原子一起，可以是含有3至6个碳原子的环烷亚基环或公式##STR3##的取代环丁烷亚基环，其中X为卤素，羟基或(较低)烷氧基，R.sup.5和R.sup.6各自独立地为氢，卤素，氨基，氨基甲酰，酰胺基，酰氧基，(较低)烷基，(较低)烯基，(较低)烷氧基，(较低)烷基氨基或(较低)烷基硫基，其中每个(较低)烷基，(较低)烷氧基，(较低)烷基氨基或(较低)烷基硫基基团可以包含1或2个从氨基，羧基，卤素和无毒药学可接受的酸盐加成物，生理可水解酯和溶剂化物中选择的取代基。其中R.sup.1为氢的化合物是强效的抗菌剂。本发明还涉及它们的制备方法。