benzhydryl 7β-(2-phenylacetamido)-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate | 123054-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: benzhydryl 7β-(2-phenylacetamido)-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate
• 英文别名: benzhydryl (6R,7R)-3-(1,3-benzothiazol-2-ylsulfanyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 123054-36-4
• 化学式: C₃₅H₂₇N₃O₄S₃
• 分子量: 649.815
• InChiKey: CDIZFSWMHSZEEW-CYTLCNBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.6
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzhydryl 7β-(2-phenylacetamido)-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate 在 吡啶 、 甲醇 、 五氯化磷 、 1-羟基苯并三唑 、 苯甲醚 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 反应 9.5h， 生成
  参考文献：
  名称：

  新型头孢菌素衍生物在3位具有双环杂环。第一部分：3-（苯并噻唑-2-基）硫代头孢菌素衍生物CP0467及其相关化合物的合成和生物学活性。

  摘要：

  合成了一系列在C-3位具有各种双环杂环的头孢菌素衍生物，并评估了其抗菌活性。其中CP0467（3a）对耐甲氧西林的金黄色葡萄球菌（MRSA）表现出优异的抗菌活性（MIC90 = 6.25 microg / mL），并且对MRSA的青霉素结合蛋白2'具有极高的亲和力（I50 = 0.49 microg / mL）。此外，3a在小鼠中显示出长效药代动力学特征（AUC（无穷大）= 482.3 microg / h / mL，T（1/2）= 1.9 h）。

  DOI：

  10.1016/s0968-0896(98)00050-9
• 作为产物：
  描述：

  Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenylacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate 在 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到benzhydryl 7β-(2-phenylacetamido)-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate
  参考文献：
  名称：

  A Novel Approach to Cephalosporins From Allenylazetidinones: A New Cyclization Strategy via Tandem Cuprate Addition-Sulfenylation

  摘要：

  An efficient approach to the synthesis of 3-substituted cephems bearing carbon-based substituents of choice at the C(3) position from inexpensive penicillins is described. The strategy involves the synthesis of an allenylazetidinone from penicillin sulfoxide followed by the addition of an organocuprate at low temperature. Organocuprates undergo 1,4-conjugate addition at the central allenic carbon of the allenylazetidinone to form a carbon-carbon bond which is followed by ring closure via an intramolecular sulfenylation reaction. The chemistry has been applied to the synthesis of a variety of 3-substituted cephems bearing substituents such as alkyl, cycloalkyl, aryl, alkenyl, and allyl. Precursors to the synthesis of important antibiotics, i.e., Cefadroxil, Cefixime, and Cefzil, are also available from this novel approach. The methodology is not limited to carbon-based 3-substituted cephems, but provides access to some 3-norcephalosporins as well.

  DOI：

  10.1021/jo00096a045

文献信息

• studies on anti-helicobacter pylori agents. part 2: new cephem derivatives
  作者：Yoshiki Yoshida、Keiji Matsuda、Hiroshi Sasaki、Yoshimi Matsumoto、Satoru Matsumoto、Shuichi Tawara、Hisashi Takasugi

  DOI：10.1016/s0968-0896(00)00163-2

  日期：2000.9

  The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of cephem derivatives are described. Introduction of thio-heterocyclic groups containing N- and S-atoms to the 3-position and phenyl or thienyl acetamido groups to the 7-position of the cephem nucleus dramatically improved the activity. From this series of derivatives, compound 13i was Found to have extremely potent in vitro anti-H. pylori activity, superior therapeutic efficacy compared to AMPC and CAM, no cross-resistance between CAM or MNZ and low potential for causing diarrhea due to instability to beta-lactamase. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A general route to 3-functionalized 3-norcephalosporins
  作者：Vittorio Farina、Stephen R. Baker、Sheila I. Hauck

  DOI：10.1021/jo00281a048

  日期：1989.9
• FARINA, VITTORIO;BAKER, STEPHEN R.;HAUCK, SHEILA I., J. ORG. CHEM., 54,(1989) N0, C. 4962-4966
  作者：FARINA, VITTORIO、BAKER, STEPHEN R.、HAUCK, SHEILA I.

  DOI：——

  日期：——