2-(fur-2-yl)-2-hydroxyiminoacetic acid | 72366-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(fur-2-yl)-2-hydroxyiminoacetic acid
• 英文别名: 2-Hydroxyimino-2-(fur-2-yl)acetic acid；2-(Fur-2-yl)-2-hydroxyiminoacetic acid；2-(furan-2-yl)-2-hydroxyiminoacetic acid
• CAS: 72366-76-8
• 化学式: C₆H₅NO₄
• 分子量: 155.11
• InChiKey: RNNIWANKYVVTII-UHFFFAOYSA-N

物化性质

• 沸点：
  371.6±34.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(fur-2-yl)-2-hydroxyiminoacetic acid 、 氯乙酰胺 以 二甲基亚砜 为溶剂， 以24%的产率得到2-aminocarbonylmethoxyimino-2-(fur-2-yl)acetic acid
  参考文献：
  名称：

  7 2-(Aminocarbonylalkoxyimino)acetamido! derivatives of cephalosporin

  摘要：

  具有以下结构的头孢菌素抗生素，其中7.beta.-acylamido基团的结构为##STR1##（其中R为苯基，噻吩基或呋喃基; R.sup.a和R.sup.b分别选自氢，C.sub.1-4烷基，C.sub.2-4烯基，C.sub.3-7环烷基，苯基，萘基，噻吩基，呋喃基，羧基，C.sub.2-5烷氧基羰基，氨基羰基，N-取代氨基羰基和氰基，或R.sup.a和R.sup.b与它们所连接的碳原子一起形成C.sub.3-7环烷基亚甲基或环烯基亚甲基基团; R.sup.c为氢或C.sub.1-4烷基; m和n各为0或1，使m和n的和为0或1），表现出广谱抗生素活性，特别是对革兰氏阴性微生物具有极高的活性，包括产生β-内酰胺酶的微生物。这些化合物是syn异构体或存在于syn和anti异构体的混合物中，其中至少90％为syn异构体，对包括吲哚阳性菌株在内的变形杆菌具有特别好的活性，尤其是当R.sup.a和R.sup.b都不是氢时，对假单胞菌具有特别好的活性。

  公开号：

  US04074047A1

文献信息

• Cephalosporins having at position-7 a carboxy substituted
  申请人：Glaxo Laboratories Limited

  公开号：US04144392A1

  公开（公告）日：1979-03-13

  Cephalosporin antibiotics having the formula: ##STR1## (where R is thienyl, furyl or phenyl; R.sup.a is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl or phenyl, and R.sup.b is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl, phenyl, carboxy or C.sub.2-5 alkoxycarbonyl, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a C.sub.3-7 cycloalkylidene or cycloalkenylidene group; R.sup.13 is C.sub.1 -C.sub.6 alkyl, C.sub.3-7 cycloalkyl, phenylalkyl, phenyl or naphthyl, thiadiazolyl, diazolyl, triazolyl, tetrazolyl, thiazolyl, thiatriazolyl, oxazolyl, oxadiazolyl, pyridyl, pyrimidyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, triazolopyridyl or purinyl, and n is 0, 1 or 2 and their physiologically acceptable derivatives exhibit broad spectrum antibiotic activity characterized by particularly high activity against gram negative microorganisms, including those which produce .beta.-lactamases. The compounds, which are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer, have particularly high in vitro activity against strains of Escherichia coli, Haemophilus influenzae and Proteus organisms; and unusually high activity against Pseudomonas organisms.

  具有以下式子的头孢菌素类抗生素：##STR1##（其中R是噻吩基，呋喃基或苯基; R.sup.a是氢，C.sub.1-4烷基，C.sub.2-4烯基，C.sub.3-7环烷基或苯基，而R.sup.b是氢，C.sub.1-4烷基，C.sub.2-4烯基，C.sub.3-7环烷基，苯基，羧基或C.sub.2-5烷氧羰基，或R.sup.a和R.sup.b与它们所连接的碳原子一起形成C.sub.3-7环烷亚甲基或环烯亚甲基基团; R.sup.13是C.sub.1-C.sub.6烷基，C.sub.3-7环烷基，苯基烷基，苯基或萘基，噻二唑基，吡唑基，三唑基，四唑基，噻唑基，噻唑三唑基，噁唑基，噁唑二唑基，吡啶基，嘧啶基，苯并咪唑基，苯并噁唑基，苯并噻唑基，三唑吡啶基或嘌呤基，n为0，1或2，它们的生理学可接受衍生物表现出广谱抗生素活性，特别是对革兰氏阴性微生物具有很高的活性，包括产生.beta.-内酰胺酶的菌株。这些化合物是同构体或存在至少90％的同构体和反异构体混合物，对大肠杆菌，流感嗜血杆菌和变形杆菌菌株具有特别高的体外活性；并且对铜绿假单胞菌具有异常高的活性。
• Improvements in or relating to cephalosporin antibiotics
  申请人：Glaxo Laboratories Limited

  公开号：US04020058A1

  公开（公告）日：1977-04-26

  Cephalosporin antibiotics of formula ##STR1## (where R is thienyl or furyl; R.sup.a and R.sup.b are each selected from hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl, phenyl, naphthyl, thienyl, furyl, carboxy, C.sub.2-5 alkoxycarbonyl and cyano, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a C.sub.3-7 cycloalkylidene or cycloalkenylidene group; m and n are each 0 or 1 such that the sum of m and n is 0 or 1; and P is hydrogen or halogen) and their non-toxic derivatives exhibit broad spectrum antibiotic activity characterized by particularly high activity against gram negative microorganisms, including those which produce .beta.-lactamases. The compounds, which are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer, have particularly high in vitro activity against strains of Escherichia coli, Haemophilus influenzae and Proteus organisms; compounds wherein at least one of R.sup.a and R.sup.b is other than hydrogen have also shown unusually high activity against Pseudomonas organisms. Important compounds of the above type include those in which the 7.beta.-acylamido group is a syn-2-carboxymethoxy-2-(fur-2-yl)acetamido, syn-2-(2-carboxyprop-2-yloxyimino)-2-(fur-2-yl)acetamido or syn-2-(1-carboxycyclopent-1-yloxyimino)-2-(fur-2-yl)acetamido group.

  头孢菌素抗生素的化学式为##STR1##（其中R为噻吩基或呋喃基；R.sup.a和R.sup.b分别选自氢、C.sub.1-4烷基、C.sub.2-4烯基、C.sub.3-7环烷基、苯基、萘基、噻吩基、呋喃基、羧基、C.sub.2-5烷氧羰基和氰基，或R.sup.a和R.sup.b与它们连接的碳原子一起形成C.sub.3-7环烷基亚甲基或环烯基亚甲基基团；m和n分别为0或1，使m和n的和为0或1；P为氢或卤素），及其无毒衍生物展现出广谱抗生素活性，特别对革兰氏阴性微生物表现出极高的活性，包括产生β-内酰胺酶的微生物。这些化合物是同构体或存在至少90%同构体的同和反异构体混合物，对大肠杆菌、流感嗜血杆菌和变形杆菌菌株表现出特别高的体外活性；其中至少有一个R.sup.a和R.sup.b不是氢的化合物也显示出对假单胞菌菌株异常高的活性。上述类型的重要化合物包括7β-酰胺基团为syn-2-羧甲氧基-2-(呋-2-基)乙酰胺基、syn-2-(2-羧基丙-2-氧基亚胺)-2-(呋-2-基)乙酰胺基或syn-2-(1-羧基环戊-1-氧基亚胺)-2-(呋-2-基)乙酰胺基的化合物。
• Penicillin antibiotics
  申请人：Glaxo Laboratories Limited

  公开号：US03936443A1

  公开（公告）日：1976-02-03

  The invention provides novel antibiotic compounds which are 6.beta.-acylamidopenam-3-carboxylic acids and non-toxic derivatives thereof, characterized in that the acylamido group has the structure ##EQU1## WHERE R is a hydrogen atom or an organic group and R.sup.a is a hydrogen atom or an acyl group. The compounds are syn isomers or exist as mixtures containing at least 75% of the syn isomer. These antibiotic compounds possess high antibacterial activity against a range of gram positive and gram negative organisms coupled with particularly high stability to .beta.-lactamases produced by various gram negative organisms. The invention is also concerned with the administration of the compounds.

  本发明提供了新型抗生素化合物，它们是6-β-酰胺基青霉烷-3-羧酸及其非毒性衍生物，其特征在于酰胺基具有以下结构：##EQU1##其中，R为氢原子或有机基团，R.sup.a为氢原子或酰基团。这些化合物是同构体或存在至少75％同构体的混合物。这些抗生素化合物对一系列革兰氏阳性和革兰氏阴性微生物具有高抗菌活性，并具有特别高的稳定性，可对各种革兰氏阴性微生物产生的β-内酰胺酶进行抵抗。本发明还涉及这些化合物的使用。
• Cephalosporins having a 7-(carboxy substituted .alpha.-etherified
  申请人：——

  公开号：US04060686A1

  公开（公告）日：1977-11-29

  3-Carbamoyloxymethyl and 3-N-methylcarbamoyloxymethyl cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##STR1## where R is thienyl, furyl or phenyl; R.sup.a is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl or phenyl, and R.sup.b is hydrogen, carboxy, C.sub.2 -C.sub.5 carbalkoxy or any of the groups designated for R.sup.a, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a C.sub.3-7 cycloalkylidene or cycloalkenylidene group; exhibit broad spectrum antibiotic activity charcterized by particularly high activity against gram negative microorganisms, including those which produce .beta.-lactamases. The compounds, which are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer, have particularly high in vitro activity against strains of Escherichia coli, Haemophilus influenzae and Proteus organisms; and also shown unusually high activity against Pseudomonas organisms.

  这是一种头孢菌素抗生素，包括3-氨基甲氧基甲基和3-N-甲基氨基甲氧基甲基头孢菌素抗生素，其中7-β-酰胺基团具有以下结构：##STR1##其中R为噻吩基、呋喃基或苯基；R.sup.a为C.sub.1-4烷基、C.sub.2-4烯基、C.sub.3-7环烷基或苯基，R.sup.b为氢、羧基、C.sub.2-C.sub.5羧基烷氧基或R.sup.a指定的任何基团，或R.sup.a和R.sup.b与它们连接的碳原子一起形成C.sub.3-7环烷亚基或环烯亚基。这些化合物表现出广谱抗生素活性，特别是对革兰氏阴性微生物的活性非常高，包括产生β-内酰胺酶的微生物。这些化合物是同构体或存在于至少90％的同构体和反构体混合物中，对大肠杆菌、流感嗜血杆菌和变形杆菌菌株的体外活性特别高，并且对假单胞菌的活性也异常高。
• 3-Carbamoyloxymethyl-7-substituted oximino acetamido cephalosporanic
  申请人：Glaxo Laboratories Limited

  公开号：US04162360A1

  公开（公告）日：1979-07-24

  3-Carbamoyloxymethyl and 3-N-methylcarbamoyloxymethyl cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##STR1## where R is thienyl, furyl or phenyl; R.sup.a is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl or phenyl, and R.sup.b is hydrogen, carboxy, C.sub.2 -C.sub.5 carbalkoxy or any of the groups designated for R.sup.a, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a C.sub.3-7 cycloalkylidene or cycloalkenylidene group; exhibit broad spectrum antibiotic activity characterized by particularly high activity against gram negative microorganisms, including those which produce .beta.-lactamases. The compounds, which are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer, have particularly high in vitro activity against strains of Escherichia coli, Haemophilus influenzae and Proteus organisms; and also shown unusually high activity against Pseudomonas organisms.

  这是有关头孢菌素抗生素的描述，其中3-氨甲酰氧甲基和3-N-甲基氨甲酰氧甲基头孢菌素抗生素的7-β-酰胺基团具有结构##STR1##其中R为噻吩基，呋喃基或苯基；R.sup.a为C.sub.1-4烷基，C.sub.2-4烯基，C.sub.3-7环烷基或苯基，而R.sup.b为氢，羧基，C.sub.2-C.sub.5羰基烷氧基或R.sup.a指定的任何基团，或R.sup.a和R.sup.b与它们附着的碳原子一起形成C.sub.3-7环烷亚基或环烯亚基。这些化合物表现出广谱抗生素活性，特别是对革兰氏阴性微生物的活性很高，包括产生β-内酰胺酶的微生物。这些化合物是同构体或存在于同构体和反异构体的混合物中，其中至少含有90％的同构体，对大肠杆菌，流感嗜血杆菌和变形杆菌菌株表现出特别高的体外活性，并且对假单胞菌菌株也显示出异常高的活性。