carbacephalosporin hydrochloride | 123932-46-7

• 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: carbacephalosporin hydrochloride
• CAS: 123932-46-7
• 化学式: C₁₅H₁₄ClN₃O₅*ClH
• 分子量: 388.207
• InChiKey: YMNSRZXNBGITEB-LYCTWNKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  carbacephalosporin hydrochloride 在 N,N-二甲基丁胺 TEA 、 氯甲酸异丁酯 作用下， 生成 氯碳头孢
  参考文献：
  名称：

  An enantioselective synthesis of loracarbef (LY163892/KT3777)

  摘要：

  DOI：

  10.1016/s0040-4039(01)80388-9
• 作为产物：
  描述：

  cis-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid, (4-nitrophenyl)methyl ester 在 Rh₂(O₂CC₇H₁₅)4 盐酸 、 (PhO)3P*Cl₂ 、 p-dodecyl-SO₂N₃ 、 TEA 作用下， 以 吡啶 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 生成 carbacephalosporin hydrochloride
  参考文献：
  名称：

  An enantioselective synthesis of loracarbef (LY163892/KT3777)

  摘要：

  DOI：

  10.1016/s0040-4039(01)80388-9

文献信息

• N5-Acetyl-N5-hydroxy-L-ornithine-derived siderophore-carbacephalosporin .beta.-lactam conjugates: iron transport mediated drug delivery
  作者：E. Kurt Dolence、Albert A. Minnick、Marvin J. Miller

  DOI：10.1021/jm00164a001

  日期：1990.2
• The synthesis and biological characteristics of new orally active cephems.
  作者：ROBERT J. TERNANSKY、CHRISTOPHER L. JORDAN、F. WILLIAM BELL、THERESEA G. SKAGGS、JEFFREY S. KASHER

  DOI：10.7164/antibiotics.46.1897

  日期：——
• Synthesis and siderophore and antibacterial activity of N5-acetyl-N5-hydroxyl-L-ornithine derived siderophore-.beta.-lactam conjugates: iron transport mediated drug delivery
  作者：E. Kurt Dolence、Albert A. Minnick、Chia En Lin、Marvin J. Miller、Shelley M. Payne

  DOI：10.1021/jm00107a014

  日期：1991.3

  N5-Acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithine, the functionally instrumental component of the albomycins and ferrichromes, has been incorporated as a ''carrier'' substructure into both carbacephalosporin and oxamazin type beta-lactam antibiotics. The previously synthesized protected version of this tripeptide (14) was coupled with various beta-lactam analogues 17, 19, 24, and 25 to give protected conjugates 21, 22, 26, and 27. Final deprotection by hydrogenolysis provided the deprotected siderophore-beta-lactam antibiotic conjugates 1-4. The growth-promoting ability of each has been evaluated using either the siderophore-deficient mutant Shigella flexneri SA 100 or S. flexneri SA240 (SA 100 iucD:Tn5). Measurement of the growth-promoting activity using two isogenic Escherichia coli strains differing only in the presence or absence of fhuA (hydroxamate ferrichrome receptor) suggests uptake by the hydroxamate iron-transport system. The antibacterial activity of these conjugates has been investigated, and the potential for use of the ferrichrome iron-transport system as a means of drug delivery is discussed.
• The synthesis of 7α-amidocarbacephems
  作者：Christina C. Bodurow、Jeffrey N. Levy、Keith W. Wiitala

  DOI：10.1016/s0040-4039(00)74239-0

  日期：1992.7

  Study of compounds related to the first clinically-investigated 7-beta-amidocarbacephem, loracarbef (1), led to the preparation of key 7-alpha-amidocarbacephem derivatives. The synthesis, characterization, and biological properties of these compounds are reported.
• Iron Transport-Mediated Drug Delivery: Synthesis and Biological Evaluation of Cyanuric Acid-Based Siderophore Analogs and .beta.-Lactam Conjugates
  作者：Manuka Ghosh、Marvin J. Miller

  DOI：10.1021/jo00084a018

  日期：1994.3

  Trihydroxamate-containing isocyanurates 4a-c were synthesized and determined to be capable of substituting for natural siderophores (microbial iron sequestering agents) in limited microbiological assays. The direct coupling of protected 4a to carbacephalosporins 16 and 17 and subsequent deprotection gave conjugates 20 and 21. The Lorabid conjugate 21 was especially active against E. coli X580 in preliminary biological tests, thus demonstrating the continued potential of siderophore-mediated drug delivery.