benzhydryl 7β-amino-3-<(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl>-3-cephem-4-carboxylate | 37059-79-3

• 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 7β-amino-3-<(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl>-3-cephem-4-carboxylate
• 英文别名: Diphenylmethyl 7beta-amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylate；benzhydryl (6R,7R)-7-amino-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 37059-79-3
• 化学式: C₂₄H₂₂N₄O₃S₃
• 分子量: 510.662
• InChiKey: OQNQWSYPXOWUHL-XMSQKQJNSA-N

物化性质

• 沸点：
  732.8±70.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzhydryl 7β-amino-3-<(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl>-3-cephem-4-carboxylate 在 potassium carbonate 、 甲基磺酰氯 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(Z)-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  7个带有C-3取代基的β-[（Z）-2-（2-氨基噻唑-4-基）-3-（取代）-2-丙烯酰基氨基] -3-头孢的合成及其构效关系。

  摘要：

  一系列7个β-[（（Z）-2-（2-氨基噻唑-4-基）-3-（取代）-2-丙烯酰基氨基] -3- Cephe m-4-羧酸的合成及生物活性描述了-3个取代及其新戊酰氧基甲基酯。这些酸化合物对革兰氏阳性和革兰氏阴性细菌均显示出有效的抗菌活性。发现该系列中所选化合物的新戊酰氧基甲基酯在小鼠中被小肠很好吸收。最终选择了新戊酰氧基甲基7β-[（（Z）-2-（2-氨基噻唑-4-基）-2-戊烯酰氨基] -3-氨基甲酰氧基甲基-3-cephem-4-羧化酶盐酸盐水合物（S-1108）用于临床评估。

  DOI：

  10.7164/antibiotics.47.466
• 作为产物：
  描述：

  diphenylmethyl 7β-(thiophen-2-acetamido)-3-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-ceph-3-em-4-carboxylate 在 甲醇 、 五氯化磷 、 水 、 N,N-二甲基苯胺 作用下， 生成 benzhydryl 7β-amino-3-<(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl>-3-cephem-4-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro antimicrobial activity of 3-heteroarylsulphonylmethyl cephems: a new class of cephalosporins

  摘要：

  A series of 3-heteroarylsulphonylmethyl and 3-heteroarylsulphenylmethyl cephems were prepared and tested for antimicrobial activities. In contrast to the adverse effect of oxidized ring sulphur of penams and cephems on antimicrobial activities, the oxidized side-chain sulphur of 3-mercaptoheteroaryl cephems retained Gram-negative and slightly decreased Gram-positive activity. The chemical nature of the moieties substituted at C-7 and C-3 positions also influenced the antibacterial activity and spectrum. Compounds with thienyl substitution at C-7 and sulphonylmethylthiazoles or sulphonylmethylthiadiazoles at C-3 exhibited good differentials in antibacterial activity vet-sus their unoxidized counterparts.

  DOI：

  10.1016/0223-5234(96)88221-3

文献信息

• Cephalosporins having (.alpha.-etherified oximino)acylamido groups at
  申请人：Glaxo Laboratories Limited

  公开号：US03971778A1

  公开（公告）日：1976-07-27

  The invention provides novel antibiotic compounds which are 7.beta.-acylamidoceph-3-em-4-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 an etherifying monovalent organic group linked to the oxygen atom through a carbon atom. 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 or 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.

  该发明提供了一种新型抗生素化合物，即7-β-酰胺基头孢-3-乙烯-4-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是氢原子或有机基团，R.sup.a是通过碳原子与氧原子连接的醚化一价有机基团。这些化合物是同构体或存在至少75％的同构体混合物。这些抗生素化合物具有高抗菌活性，可对一系列革兰氏阳性和革兰氏阴性微生物产生高度的稳定性，其尤其对各种革兰氏阴性微生物产生的β-内酰胺酶具有高度的稳定性。该发明还涉及该化合物的给药。
• Syn isomers of cephalosporins having .alpha.-hydroximino- or
  申请人：Glaxo Laboratories Limited

  公开号：US04209616A1

  公开（公告）日：1980-06-24

  The invention provides novel antibiotic compounds which are 7.beta.-acylamidoceph-3-em-4-carboxylic acids, and non-toxic derivatives thereof, and 6.beta.-acylamidopenam-3-carboxylic acids, and non-toxic derivatives thereof, characterized in that the acylamido group has the structure ##STR1## 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.

  本发明提供了新的抗生素化合物，它们是7-β-酰胺基头孢-3-酰基-4-羧酸和其非毒性衍生物，以及6-β-酰胺基青霉烷-3-羧酸和其非毒性衍生物，其特征在于酰胺基具有以下结构：##STR1## 其中R是氢原子或有机基团，R.sup.a是氢原子或酰基。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度的抗菌活性，并具有特别高的稳定性，能够抵抗各种革兰氏阴性微生物产生的β-内酰胺酶。本发明还涉及该化合物的使用。
• 3-Hydroxymethyl-7.beta.-(2-alkoxy-or
  申请人：Glaxo Laboratories Limited

  公开号：US04033950A1

  公开（公告）日：1977-07-05

  The invention provides novel antibiotic compounds which are 7.beta.-acylamidoceph-3-em-4-carboxylic acids, and non-toxic derivatives thereof characterized in that the acylamido group has the structure ##STR1## where R is a hydrogen atom or an organic group and R.sup.a is an etherifying monovalent organic group linked to the oxygen atom through a carbon atom. 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.

  本发明提供了一种新型抗生素化合物，它们是7.beta.-acylamidoceph-3-em-4-carboxylic酸及其非毒性衍生物，其特征在于酰胺基团具有以下结构：##STR1##其中R是氢原子或有机基团，R.sup.a是通过碳原子连接到氧原子的醚化一价有机基团。这些化合物是同构体或存在至少75％的同构体混合物。这些抗生素化合物对一系列革兰氏阳性和阴性菌具有高抗菌活性，并具有特别高的稳定性，能够对各种革兰氏阴性菌产生的β-内酰胺酶进行抑制。本发明还涉及这些化合物的给药。
• 3-Acetoxym
  申请人：Glaxo Laboratories Limited

  公开号：US04064346A1

  公开（公告）日：1977-12-20

  The invention provides novel antibiotic compounds which are 7.beta.-acylamidoceph-3-em-4-carboxylic acids, and non-toxic derivatives thereof characterized in that the acylamido group has the structure ##STR1## where R is a hydrogen atom or an organic group and R.sup.a is an etherifying monovalent organic group linked to the oxygen atom through a carbon atom. 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7.beta.-酰胺基头孢-3-乙烯-4-羧酸及其非毒性衍生物，其特征在于酰胺基具有以下结构：##STR1## 其中R是氢原子或有机基团，R.sup.a是通过碳原子与氧原子连接的醚化一价有机基团。这些化合物是同构体或存在至少75％的同构体混合物。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度的抗菌活性，同时对各种革兰氏阴性微生物产生的β-内酰胺酶具有特别高的稳定性。本发明还涉及化合物的使用方法。
• Cephalosporins having (.alpha.-etherified oximino) acylamido groups at
  申请人：Glaxo Laboratories Limited

  公开号：US04079178A1

  公开（公告）日：1978-03-14

  The invention provides novel antibiotic compounds which are 7.beta.-acylamidoceph-3-em-4-carboxylic acids, and non-toxic derivatives thereof characterized in that the acylamido group has the structure ##STR1## WHERE R is a hydrogen atom or an organic group and R.sup.a is an etherifying monovalent organic group linked to the oxygen atom through a carbon atom. 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 or 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.

  该发明提供了新型抗生素化合物，它们是7-β-酰胺基头孢-3-烯-4-羧酸，以及其非毒性衍生物，其特征在于酰胺基具有结构##STR1##其中R是氢原子或有机基团，R.sup.a是通过碳原子连接到氧原子的醚化一价有机基团。这些化合物是同构体或存在至少75％的同构体混合物。这些抗生素化合物具有高抗菌活性，对一系列革兰氏阳性和革兰氏阴性菌具有高度稳定性，特别是对多种革兰氏阴性菌产生的β-内酰胺酶具有高度稳定性。该发明还涉及该化合物的使用。