benzhydryl 7-aminocephalocporonate | 27266-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzhydryl 7-aminocephalocporonate
• 英文别名: 7-amino-3-acetoxymethyl-ceph-3-em-4-carboxylic acid benzhydryl ester；benzhydrol 7-amino-3-acetoxy-methyl-ceph-3-em-4-carboxylate；Benzhydryl 7-amino-3-acetoxymethyl-3-cephem-4-carboxylate；7-Amino-cephalosporansaeure-benzhydrylester；Benzhydryl 3-acetoxymethyl-7-amino-ceph-3-eme-4-carboxylate；benzhydryl (6R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 27266-61-1；54600-89-4
• 化学式: C₂₃H₂₂N₂O₅S
• 分子量: 438.504
• InChiKey: SYPOLUBDFBZUAI-LMNIDFBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzhydryl 7-aminocephalocporonate 在 亚硝酸异丙酯 、 异丙基氯化镁 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.42h， 生成 benzhydryl 7-[(Z)-bromomethylidene]cephalosporanate
  参考文献：
  名称：

  Catalytic Approaches to the Synthesis of β-Lactamase Inhibitors

  摘要：

  Catalytic couplings were utilized to stereospecifically synthesize several 7E- and 7Z-alkylidenecephalosporins. Members of this class are known inhibitors of beta-lactamase. Zinc/NH4Cl reduction of dibromide 14 stereospecifically produced E-monobromide, 15. In contrast, treatment of 14 with isopropylmagnesium bromide, followed by mild acid, stereospecifically produced Z-monobromide 27. These reactions involves table, intermediate alpha-(metalloalkylidene)-beta-lactams. Monobromides 15 and 27 were stereo specific ally coupled to organostannanes, or were converted to the corresponding organostannanes, 22 and 32, which coupled with organohalides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00426-9

文献信息

• Method for preserving quaternary ammonium salt
  申请人：——

  公开号：US20030153785A1

  公开（公告）日：2003-08-14

  A method of improving the stability of a quaternary ammonium salt and a method of efficiently preparing the quaternary ammonium salt having improved stability.

  一种提高季铵盐稳定性的方法和一种高效制备稳定性提高的季铵盐的方法。
• 7-(2-Amino-4-thiazolyl)-acetamido cephalosporanic acids
  申请人：Roussel Uclaf

  公开号：US04426519A1

  公开（公告）日：1984-01-17

  Novel syn isomers of 7-(2-amino-4-thiazolyl)-acetamido-cephalosporanic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of --(CH.sub.2).sub.n --S--R.sub.2, --CHF.sub.2 and --(CH.sub.2).sub.n --S--CN, R.sub.2 is selected from the group consisting of optionally protonated ##STR2## n is an integer from 1 to 4, R.sub.1 is selected from the group consisting of hydrogen, chlorine, methoxy, alkyl and alkylthio of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms, azidomethyl, acetoxymethyl, carbamoyloxymethyl, ##STR3## and --CH.sub.2 --S--R', Alk is alkyl of 1 to 4 carbon atoms, R' is selected from the group consisting of an optionally substituted nitrogen containing heterocycle and an acyl of an aliphatic acid of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen and an easily cleavable ester and when R is --(CH.sub.2).sub.n --SR.sub.2, the COOA group may be the anion --COO-- and when R is --(CH.sub.2).sub.n --SCN or --CHF.sub.2, A may further be selected from the group consisting of an equivalent of an alkali metal, an alkaline earth metal, magnesium, --NH.sub.4 and a non-toxic, pharmaceutically acceptable organic amine and their non-toxic, pharmaceutically acceptable acid addition salts having antibiotic properties and a novel process and novel intermediates for their preparation.

  这是一段关于7-(2-氨基-4-噻唑基)-乙酰胺头孢菌素化合物的新型同分异构体的描述。该化合物的结构式为##STR1##其中R选自--(CH.sub.2).sub.n --S--R.sub.2，--CHF.sub.2和--(CH.sub.2).sub.n --S--CN的群体，R.sub.2选自可选质子化的##STR2##，n为1至4的整数，R.sub.1选自1至5个碳原子的氢、氯、甲氧基、烷基和烷基硫代基、3至5个碳原子的环烷基、偶氮甲基、乙酰氧甲基、氨甲酰氧甲基、##STR3##和--CH.sub.2 --S--R'，Alk为1至4个碳原子的烷基，R'选自可选取代的含氮杂环和2至4个碳原子的脂肪酸酰基的群体，A选自氢和易于分解的酯的群体，当R为--(CH.sub.2).sub.n --SR.sub.2时，COOA基团可以是阴离子--COO--，当R为--(CH.sub.2).sub.n --SCN或--CHF.sub.2时，A还可以选自等效的碱金属、碱土金属、镁、--NH.sub.4和非毒性、药学上可接受的有机胺及其非毒性、药学上可接受的酸盐，具有抗生素性能，以及制备它们的新型过程和新型中间体。
• Oximes
  申请人：Roussel Uclaf

  公开号：US04439433A1

  公开（公告）日：1984-03-27

  Novel oximes of the syn isomers of 7-[2-(2-amino-4-thiazolyl)-acetamido]ceph-3-eme-4-carboxylic acid compounds of the fomrula ##STR1## wherein B is --(CH.sub.2).sub.n' --R.sub.5, n' is an integer from 1 to 4, R.sub.5 is ##STR2## R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and when taken together with the nitrogen to which they are attached are selected from the group consisting of phthalimido and 1-pyridinyl, R.sub.1 is selected from the group consisting of chloro, CH.sub.3 O--, alkyl and alkylthio of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms, --CH.sub.2 --S--R.sub.12, acetoxymethyl, carbamoyloxymethyl and ##STR3## R.sub.12 is selected from the group consisting of 2-oxo-(3H)-thiazolin-4-yl-carbonyl, 3-methyl-1,2-oxazol-5-yl-carbonyl, acyl of an alkanoic acid of 2 to 4 carbon atoms and a nitrogen heterocycle, Alka is alkyl of 1 to 4 carbon atoms and A is selected from the group consisting of hydrogen, --NH.sub.4, alkali metal, alkaline earth metal, magnesium, a non-toxic, pharmaceutically acceptable organic amine and easily cleaved ester and their non-toxic, pharmaceutically acceptable acid addition salts; having antibacterial activity and novel intermediates therefore.

  化合物的新型氧肟类似物，其为式子##STR1##的7-[2-(2-氨基-4-噻唑基)-乙酰胺基]头孢-3-酰基-4-羧酸化合物的同构体，其中B为--(CH.sub.2).sub.n' --R.sub.5，n'为1到4的整数，R.sub.5为##STR2## R.sub.6和R.sub.7分别选自氢和1到4个碳原子的烷基组成的群，当它们与它们所连接的氮一起被选自邻苯二甲酰亚胺和1-吡啶基的群时，R.sub.1选自氯，CH.sub.3 O--，1到5个碳原子的烷基和烷基硫醚，3到5个碳原子的环烷基，--CH.sub.2 --S--R.sub.12，醋酸甲氧甲基，氨甲酰氧甲基和##STR3## R.sub.12选自2-氧代-(3H)-噻唑烷-4-基-羰基，3-甲基-1,2-噁唑-5-基-羰基，2到4个碳原子的脂肪酸酰基和一个氮杂环，Alka为1到4个碳原子的烷基，A选自氢，--NH.sub.4，碱金属，碱土金属，镁，一种无毒的、药学上可接受的有机胺和容易被水解的酯及其无毒、药学上可接受的酸盐；具有抗菌活性和新型中间体。
• Novel 7-(2-amino-4-thiazolyl)-acetamido-cephalosporanic acids
  申请人：Roussel Uclaf

  公开号：US04328225A1

  公开（公告）日：1982-05-04

  Novel syn isomers of 7-(2-amino-4-thiazolyl)-acetamido-cephalosporanic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of --(CH.sub.2).sub.n --S--R.sub.2, --CHF.sub.2 and --(CH.sub.2).sub.n --S--CN, R.sub.2 is selected from the group consisting of optionally protonated ##STR2## n is an integer from 1 to 4, R.sub.1 is selected from the group consisting of hydrogen, chlorine, methoxy, alkyl and alkylthio of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms, azidomethyl, acetoxymethyl, carbamoyloxymethyl, ##STR3## and --CH.sub.2 --S--R', Alk is alkyl of 1 to 4 carbon atoms, R' is selected from the group consisting of an optionally substituted nitrogen containing heterocycle and an acyl of an aliphatic acid of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen and an easily cleavable ester and when R is --(CH.sub.2).sub.n --SR.sub.2, the COOA group may be the anion --COO.sup.- and when R is --(CH.sub.2).sub.n --SCN or --CHF.sub.2, A may further be selected from the group consisting of an equivalent of an alkali metal, an alkaline earth metal, magnesium, --NH.sub.4 and a non-toxic, pharmaceutically acceptable organic amine and their non-toxic, pharmaceutically acceptable acid addition salts having antibiotic properties and a novel process and novel intermediates for their preparation.

  这是一种新型的7-(2-氨基-4-噻唑基)-乙酰胺-头孢菌素酸化合物的同分异构体，其化学式为##STR1##其中R从群组中选择--(CH.sub.2).sub.n --S--R.sub.2，--CHF.sub.2和--(CH.sub.2).sub.n --S--CN，R.sub.2从群组中选择可选择质子化的##STR2##n是1到4的整数，R.sub.1从群组中选择氢，氯，甲氧基，1到5个碳原子的烷基和烷基硫醚，3到5个碳原子的环烷基，偶氮基甲基，乙酰氧甲基，羰酰氧甲基，##STR3##和--CH.sub.2 --S--R'，Alk是1到4个碳原子的烷基，R'从群组中选择可选择取代的含氮杂环和2到4个碳原子的脂肪酸酰基，A从群组中选择氢和易于分解的酯，当R为--(CH.sub.2).sub.n --SR.sub.2时，COOA基团可以是阴离子--COO.sup.-，当R为--(CH.sub.2).sub.n --SCN或--CHF.sub.2时，A还可以从群组中选择相当于碱金属，碱土金属，镁，--NH.sub.4和一种无毒的、药学上可接受的有机胺及其无毒的、药学上可接受的酸加合物，具有抗生素属性，以及它们的制备的新工艺和新中间体。
• Cephem compounds, and their production, and medicaments containing them
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0112164A2

  公开（公告）日：1984-06-27

  A cephem compound represented by the general formula I wherein R represents a C, to C5 alkyl group which may be substituted by a C1 to C5 acyloxy group; a C, to C5 alkyl-thio group; wherein R. represents a hydrogen atom or a C, to C5 alkyl group; wherein Rb represents a hydrogen atom, (CH2)mCOOH, (CH2)mOH, (CH2)mNH2, (CH2)mSO3H, or COHN-R' and where R' represents a hydrogen atom, a hydroxy group, or (CH2)nCOOH, m represents 0 or an integer of 1 to 3; and n represents an integer of 1 to 3. The cephem compounds according to the invention may be used as a prophylaxis and treatment for bacterial infectious diseases.

  由通式 I 所代表的头孢菌素化合物 其中 R 代表可被 C1 至 C5 乙酰氧基取代的 C 至 C5 烷基；C 至 C5 硫代烷基；其中 R. 代表氢原子或 C 至 C5 烷基；其中 Rb 代表氢原子、(CH2)mCOOH、( )mOH、( )mNH2、( )mSO3H 或 COHN-R'；其中 R' 代表氢原子、羟基或 ( )nCOOH，m 代表 0 或 1 至 3 的整数；n 代表 1 至 3 的整数。 根据本发明的头孢菌素化合物可用作细菌感染性疾病的预防和治疗。