6β-(4-nitro-benzoylamino)-penicillanic acid | 17028-71-6

• 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: 6β-(4-nitro-benzoylamino)-penicillanic acid
• 英文别名: '(p-Nitro-phenyl)-penicillin'；(4-nitro-phenyl)-penicillin；(2S,5R,6R)-3,3-dimethyl-6-[(4-nitrobenzoyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 17028-71-6
• 化学式: C₁₅H₁₅N₃O₆S
• 分子量: 365.367
• InChiKey: PSWRXQGMOSCWMW-GBIKHYSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6β-(4-nitro-benzoylamino)-penicillanic acid 在 glycine buffer 作用下， 生成
  参考文献：
  名称：

  摘要：

  The kinetics of acid hydrolysis of phenylpenicillins substituted in the benzene ring were studied at pH 3.0 and temperatures of 20, 25, and 30degreesC. A Hammett correlation analysis of the reaction was performed.

  DOI：

  10.1023/a:1016172722206
• 作为产物：
  描述：

  6-β-aminopenicillanic acid sodium salt 、 对硝基苯甲酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 6β-(4-nitro-benzoylamino)-penicillanic acid
  参考文献：
  名称：

  使用二环己基碳二亚胺作为缩合剂合成青霉素。

  摘要：

  DOI：

  10.1021/jm50017a015

文献信息

• Kinetic Approach to the Development in β-Lactam Antibiotics. I. Comparative Stability of Semisynthetic Penicillins and 6-Aminopenicillanic Acid in Aqueous Solution
  作者：TSUKINAKA YAMANA、AKIRA TSUJI、YUZO MIZUKAMI

  DOI：10.1248/cpb.22.1186

  日期：——

  The kinetics of the hydrolyses of carbenicillin, sulbenicillin, propicillin, cyclacillin, 6-(α-toluenesulfonamido)-penicillanic acid (TSPA), the substituted phenylpenicillins and 6-aminopenicillanic acid (6-APA) were studied over wide pH ranges at 35° and μ=0.5. For the hydrolysis of penicillins, the psuedo first-order rate constants, kpH at zero buffer concentration were formulated as the equation : kpH=(kH [H3O+]+k0)ƒHP+(k'0+k'OH [OH-])ƒp-, where ƒHP and ƒp- are the fractions of free-acid penicillin (HP) and ionized penicillin (P-), respectively. These catalytic rate constants were compared with those reported previously for other penicillins. The activation parameters were also determined for some penicillins. In acidic solution, penicillins except TSPA were confirmed to be hydrolyzed to the penicillenic acids via hydronium ion-catalyzed rearrangement of HP the (kH) and spontaneous rearrangement of HP (k0). The Hammett plots for kH and k0 of the substituted phenylpenicillin series gave excellent linear correlations with both ρ=-1.60. The magnitude and sign of the ρ values were consistent with the intramolecular catalyzed mechanism by the neighboring side-chain amido groups. The hydrolysis of 6-APA was found to follow first-order kinetics at low initial concentration in the range of 0.005-0.01M. From the log kpH-pH profile and the pertinent primary salt effects, the possible mechanisms for the acidic hydrolysis of 6-APA were discussed. The activation parameters were evaluated at each reaction region. At pH 5, 6-APA was found to be hydrolyzed 3-6 times faster than relatively acid-stable penicillins, which may be attributed to the inductive effect by the protonated 6-amino group. The k'0 and k'OH values were nearly the same in the hydrolyses of all penicillins and 6-APA. It can be concluded that the basic and neutral hydrolyses of these compounds are, respectively, simple hydroxide catalyzed and water catalyzed reactions.

  对氯唑西林、磺胺噻唑、西氟噻唑、环氟噻唑、6-(α-甲苯磺酰氨基)-青霉素酸（TSPA）、取代苯基青霉素和6-氨基青霉素酸（6-APA）的水解动力学在35°C及μ=0.5的广泛pH范围内进行了研究。对于青霉素的水解，零缓冲浓度下的伪一级速率常数kpH被制定为以下方程：kpH=(kH [H3O+]+k0)ƒHP+(k'0+k'OH [OH-])ƒp-，其中ƒHP和ƒp-分别是游离酸性青霉素（HP）和离子化青霉素（P-）的分数。这些催化速率常数与之前报道的其他青霉素进行了比较。一些青霉素的活化参数也被测定。在酸性溶液中，除了TSPA外的青霉素被确认通过氢离子催化的HP重排（kH）和HP的自发重排（k0）水解为青霉酰酸。取代苯基青霉素系列的kH和k0的汉密特图呈现出ρ=-1.60的优秀线性相关性。ρ值的大小和符号与邻近侧链酰胺基团的分子内催化机制一致。6-APA的水解在初始浓度为0.005-0.01M的低浓度下表现出一级动力学。从log kpH-pH的图谱和相关的初级盐效应中讨论了6-APA酸性水解的可能机制。每个反应区域的活化参数被评估。在pH 5时，发现6-APA的水解速度比相对耐酸的青霉素快3-6倍，这可能归因于质子化的6-氨基团的诱导效应。所有青霉素及6-APA的水解中，k'0和k'OH值几乎相同。可以得出结论，这些化合物的碱性和中性水解分别是简单的氢氧根催化和水催化反应。
• Enzymic hydrolysis of phenylpenicillins
  作者：M. V. Solovskii、M. V. Zhukova、E. F. Panarin

  DOI：10.1007/bf00777794

  日期：1978.9
• Cupric Ion-Catalyzed Hydrolysis of Penicillins: Mechanism and Site of Complexation
  作者：W.A. Cressman、E.T. Sugita、J.T. Doluisio、P.J. Niebergall

  DOI：10.1002/jps.2600581210

  日期：1969.12
• US3947465A
  申请人：——

  公开号：US3947465A

  公开（公告）日：1976-03-30
• US4007168A
  申请人：——

  公开号：US4007168A

  公开（公告）日：1977-02-08