(Z)-2-(ethoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetic acid | 64486-00-6

• 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: (Z)-2-(ethoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetic acid
• 英文别名: (Z)-(2-triphenylmethylaminothiazol-4-yl)ethoxyiminoacetic acid；(Z)-2-(ethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid；2,Z-Ethoxyimino-2-(2-triphenylmethylaminothiazol-4-yl)acetic acid；2-(2-tritylaminothiazol-4-yl)-(Z)-2-ethoxyiminoacetic acid；(Z)-ethoxyimino-(2-tritylamino-thiazol-4-yl)-acetic acid；(Z)-2-(2-N-tritylaminothiazol-4-yl)-2-ethoxyiminoacetic acid；(Z)-2-(2-tritylaminothiazol-4-yl)-2-ethoxyiminoacetic acid；2-(Z)-ethoxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid；(2Z)-2-ethoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid
• CAS: 64486-00-6
• 化学式: C₂₆H₂₃N₃O₃S
• 分子量: 457.553
• InChiKey: LWRXBZDYMOWJEV-FAJYDZGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (Z)-2-(ethoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetic acid 在 吡啶 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetyl]amino]-3-[[1-(methylamino)pyridin-1-ium-4-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Structure-activity Relationships within a Series of C(7)-Substitutedoxyiminocephalosporins Containing the C(3)-Methylaminopyridiniumthiomethyl Substituent. Synthesis and Biological Properties of BRL 57342 and Some Close Analogues.

  摘要：

  (6R,7R)-7-[2-(2-氨基-4-噻唑基)-2-[(Z)-[(S)-羧基(3,4-二羟基苯基)甲基]氧亚氨基]乙酰氨基]-3-(l-甲基氨基吡啶-4-硫甲基)头孢-3-em-4-甲酸钠盐（BRL 57342，1f）对革兰氏阳性菌和革兰氏阴性菌（包括铜绿假单胞菌和不动杆菌）具有极佳的体外抗菌效力。铜绿假单胞菌和不动杆菌属等革兰氏阳性和革兰氏阴性细菌的体外抗菌效力、对广谱β-内酰胺酶具有出色的稳定性。体内药效研究也反映了这种效力。

  DOI：

  10.7164/antibiotics.48.417
• 作为产物：
  描述：

  ethyl (Z)-2-(ethoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetate 生成 (Z)-2-(ethoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetic acid
  参考文献：
  名称：

  KAMACHI, HAJIME;OKUMURA, JUN;NAITO, TAKAYUKI;OKA, MASAHISA;YAMASHITA, HAR+

  摘要：

  DOI：

文献信息

• 3-(Optionally substituted-but-1-en-3-ynyl) cephalosporins
  申请人：Glaxo Group Limited

  公开号：US04666899A1

  公开（公告）日：1987-05-19

  Compounds of general formula I ##STR1## (wherein R represents NH.sub.2 -- or an acylated or silylated amino group; R.sup.2 represents a hydrogen, halogen, alkyl, aryl, carboxyl or lower alkoxycarbonyl group; R.sup.3 is hydrogen or a carboxyl blocking group; B is >Sor>S.fwdarw.O (.alpha.- or .beta.-); and the dotted line represents .DELTA..sup.2 or .DELTA..sup.3 unsaturation) and salts, solvates and esters thereof are described. Compounds where R.sup.3 is hydrogen, the dotted line represents .DELTA..sup.3 unsaturation and R is a group of formula ##STR2## (where R.sup.a is an optionally substituted heterocyclic aryl group having one or more hetero atoms selected from S, N and O in the ring, R.sup.b is an optionally substituted aryl group, R.sup.c is hydrogen, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.d is as defined for R.sup.a or is an optionally substituted group and X is amino, hydroxyl, acylated hydroxyl, carboxyl or esterified carboxyl) and especially the compounds in which B is >S, have valuable antibiotic activities. Compounds in which the --CH.dbd.CH--C.tbd.C--R.sup.2 group is in the trans configuration have been found to have good oral absorption. The remaining compounds of formula (I) are valuable as intermediates in processes for the preparation of the above active antibiotics, which processes are also described.

  通式I的化合物##STR1##（其中R代表NH.sub.2-或酰化或硅烷化氨基团；R.sup.2代表氢、卤素、烷基、芳基、羧基或较低的烷氧羰基团；R.sup.3是氢或羧基阻断基团；B是>S或>S.fwdarw.O（α-或β-）；虚线代表.DELTA..sup.2或.DELTA..sup.3不饱和度）及其盐、溶剂合物和酯已被描述。其中R.sup.3为氢，虚线代表.DELTA..sup.3不饱和度，R为通式##STR2##的一个基团（其中R.sup.a是一个可选择的取代的杂环芳基团，在环中有一个或多个来自S、N和O的杂原子，R.sup.b是一个可选择的取代的芳基团，R.sup.c是氢、酰基、烷基、烯基、炔基、环烷基、环烷基烷基、芳基或芳基烷基，R.sup.d如R.sup.a定义或是一个可选择的取代基团，X是氨基、羟基、酰化羟基、羧基或酯化羧基）以及特别是其中B是>S的化合物具有有价值的抗生素活性。已发现具有--CH.dbd.CH--C.tbd.C--R.sup.2基团的反式构型的化合物具有良好的口服吸收。通式（I）的其余化合物作为制备上述活性抗生素的过程中的中间体具有价值，这些过程也已被描述。
• 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。
• Reactive thiophosphate derivatives of thia(dia)zole acetic acid and
  申请人：Lucky, Ltd.

  公开号：US05502200A1

  公开（公告）日：1996-03-26

  The present invention relates to a novel reactive thiophosphate derivative of thia(dia)zole acetic acid which can be very effectively used in the preparation of .beta.-lactam antibiotics, and which is represented by the following general formula (I): ##STR1## in which R.sup.1 represents hydrogen or an amino-protecting group; R.sup.2 represents hydrogen, C.sub.1 -C.sub.4 alkyl, or --C(R.sup.a)(R.sup.b)CO.sub.2 R.sup.c, wherein R.sup.a and R.sup.b are identical or different from each other and represent hydrogen or C.sub.1 -C.sub.4 alkyl, or R.sup.a and R.sup.b together with a carbon atom to which they are bound can form a C.sub.3 -C.sub.7 cycloalkyl group and R.sup.c is hydrogen or a carboxy-protecting group; R.sup.3 represents C.sub.1 -C.sub.4 alkyl or phenyl or R.sup.3 together with an oxygen atom and a phosphorus atom to which it is bound can form a 5- or 6-membered heterocyclic ring; and Q represents N or CH, and to a process for preparing the same.

  本发明涉及一种新型的噻（二）唑乙酸反应性硫代磷酸酯衍生物，可非常有效地用于制备β-内酰胺类抗生素，其通式如下（I）：其中R1代表氢或氨基保护基；R2代表氢、C1-C4烷基或--C（R.sup.a）（R.sup.b）CO2R.sup.c，其中R.sup.a和R.sup.b相同或不同，代表氢或C1-C4烷基，或R.sup.a和R.sup.b连同其所连接的碳原子可以形成C3-C7环烷基，R.sup.c代表氢或羧基保护基；R3代表C1-C4烷基或苯基，或R3连同其所连接的氧原子和磷原子可以形成5-或6-成员杂环环；Q代表N或CH，以及其制备方法。
• 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。