benzylpenicillin | 496809-25-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzylpenicillin
• 英文别名: penicillin G；penicillin；6β-(2-phenyl-acetylamino)-penicillanic acid；penicillin-II；penicillin-G；(5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 496809-25-7
• 化学式: C₁₆H₁₈N₂O₄S
• 分子量: 334.396
• InChiKey: JGSARLDLIJGVTE-YXHCSQSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzylpenicillin 在 乙酸丁酯 、 磷酸 、 penicillin acylase from E_. coli 作用下， 以 水 为溶剂， 生成 6β-aminopenicillanic acid 、 苯乙酸
  参考文献：
  名称：

  Enzymatic hydrolysis of β-lactam antibiotics at low pH in a two-phase "aqueous solution - water-immiscible organic solvent" system

  摘要：

  建议使用两相“水溶液-不溶于水的有机溶剂”系统进行水解，而不是有效的生物催化合成。在pH 3-4的两相水-丁酸酯系统中，建议将苄青霉素和N-苯乙酰基去乙酰氧头孢烯酸酯酶解为相应的抗生素核6-氨基青霉烷酸和7-氨基去乙酰氧头孢烯酸。这是一种替代在碱性介质中进行生物催化水解的方法。进行了实验研究并开发了一个模型，描述了pH、相体积比、热力学常数和初始抗生素浓度对其在两相“水溶液-不溶于水的有机溶剂”系统中水解效率的影响。在两相水溶液-不溶于水的有机溶剂系统中低pH下对青霉素G和7-苯乙酰基去乙酰氧头孢烯酸的水解进行了热力学评估，显示出很高的实际潜力。建议的方法允许在将天然β-内酰胺类抗生素转化为半合成类似物的过程中排除几个工艺步骤：从丁酸酯中碱性提取生物合成抗生素，然后在pH 7.5-8.0下进行其酶解，进一步酸化反应混合物，从而导致抗生素核的沉淀。实验观察还揭示了这个过程的一个特定特征：抗生素核的动力学过饱和会减缓达到平衡的速度，应在进一步开发这种方法时予以考虑。关键词：酶解、β-内酰胺类抗生素核、两相系统、过饱和、青霉素酰化酶。

  DOI：

  10.1139/v02-096
• 作为产物：
  描述：

  (N-phenylmethanesulfonamido)methyl (2S,5R,6R)-1-aza-3,3-dimethyl-7-oxo-6-phenylacetamido-4-thiabicyclo[3.2.0]heptane-2-carboxylate 以 acetate buffer 为溶剂， 生成 benzylpenicillin
  参考文献：
  名称：

  酰氧基甲基作为药物保护基。第7部分：苄青霉素的叔磺酰胺基甲基酯前药：化学水解和抗菌活性。

  摘要：

  合成了苄青霉素（4）的叔磺酰胺基甲基酯，并将其评估为β-内酰胺抗生素的一类新的潜在前药。用HPLC研究了它们在水性缓冲液中的水解，并揭示了一个U形pH速率分布图，其pH依赖性过程从ca开始延伸。pH 2至 pH10。该途径的特征在于动力学数据，该动力学数据与涉及限速亚胺离子形成和青霉素排出的单分子机理相符。苄青霉素和相应的磺酰胺是检测和分离出的最终产物，表明β-内酰胺开环比酯水解慢得多。如从高反应性所期望的，苄青霉素酯（4）在体外具有与苄青霉素本身相似的抗菌活性。与苄青霉素衍生物相比，

  DOI：

  10.1016/s0968-0896(00)00099-7

文献信息

• COMPOSITION FOR HARDENING SOFT TISSUE
  申请人：THE CATHOLIC UNIVERSITY OF KOREA INDUSTRY-ACADEMIC COOPERATION FOUNDATION

  公开号：US20190315770A1

  公开（公告）日：2019-10-17

  The present invention relates to various compounds capable of temporarily hardening soft tissue for surgical suturing of the soft tissue. The compounds according to the present invention can temporarily increase the hardness or tension of soft tissue, thereby improving the suturing efficiency during suturing of the soft tissue, thereby preventing aftereffects or the like from occurring due to insufficient anastomosis. In addition, the compounds according to the present invention can temporarily increase the hardness or tension of soft tissue, particularly pancreas, thereby increasing the suturing efficiency during pancreaticoduodenectomy and effectively preventing pancreatic leakage.

  本发明涉及各种能够暂时硬化软组织以进行软组织缝合的化合物。根据本发明的化合物可以暂时增加软组织的硬度或张力，从而在缝合软组织时提高缝合效率，防止由于吻合不足而产生的后遗症或类似问题的发生。此外，根据本发明的化合物可以暂时增加软组织，特别是胰腺的硬度或张力，从而在胰十二指肠切除术期间提高缝合效率并有效预防胰液漏出。
• THE USE OF LIPOPHILIC BETA-LACTAM ANTIBIOTICS AND CARBOXYLATE ESTERS FOR THE TREATMENT OF BACTERIAL INFECTIONS WITHIN CITRUS AND OTHER PLANT SPECIES
  申请人：BOARD OF REGENTS OF THE NEVADA SYSTEM OF HIGHER EDUCATION ON BEHALF OF NEVADA

  公开号：US20200230114A1

  公开（公告）日：2020-07-23

  Disclosed is method for converting a beta-lactam antibiotic into a “masked” beta-lactam antibiotic to permit it to cross the waxy cuticle of a plant and then subsequently unmasking the beta-lactam and converting it into an active beta-lactam antibiotic in the plant phloem. The method permits the use of beta-lactam antibiotics to be used to treat a variety of plant bacterial infections that was not previously possible because the native beta-lactam antibiotics cannot cross the waxy cuticle of plants. In one embodiment the disclosure finds special use in the treatment of bacterial infection of citrus plants with Huanglongbing disease.

  揭示了一种将β-内酰胺类抗生素转化为“掩蔽”β-内酰胺类抗生素的方法，以允许其穿过植物的蜡质外皮，然后随后揭示β-内酰胺并将其转化为植物韧皮部中的活性β-内酰胺类抗生素。该方法允许使用β-内酰胺类抗生素来治疗多种植物细菌感染，这是以前不可能的，因为天然的β-内酰胺类抗生素无法穿过植物的蜡质外皮。在一个实施例中，该公开发现在治疗柑橘植物黄龙病细菌感染方面具有特殊用途。
• Composition for hardening soft tissue
  申请人：THE CATHOLIC UNIVERSITY OF KOREA INDUSTRY-ACADEMIC COOPERATION FOUNDATION

  公开号：US10745417B2

  公开（公告）日：2020-08-18

  The present invention relates to various compounds capable of temporarily hardening soft tissue for surgical suturing of the soft tissue. The compounds according to the present invention can temporarily increase the hardness or tension of soft tissue, thereby improving the suturing efficiency during suturing of the soft tissue, thereby preventing aftereffects or the like from occurring due to insufficient anastomosis. In addition, the compounds according to the present invention can temporarily increase the hardness or tension of soft tissue, particularly pancreas, thereby increasing the suturing efficiency during pancreaticoduodenectomy and effectively preventing pancreatic leakage.

  本发明涉及能够暂时硬化软组织的各种化合物，用于软组织的外科缝合。根据本发明的化合物可以暂时增加软组织的硬度或张力，从而在缝合软组织时提高缝合效率，防止因吻合不足而产生后遗症等。此外，根据本发明的化合物可以暂时增加软组织尤其是胰腺的硬度或张力，从而提高胰十二指肠切除术的缝合效率，有效防止胰腺渗漏。
• Composition for Hardening Soft Tissue
  申请人：The Catholic University of Korea Industry-Academic Cooperation Foundation

  公开号：US20200339601A1

  公开（公告）日：2020-10-29

  The present invention relates to various compounds capable of temporarily hardening soft tissue for surgical suturing of the soft tissue. The compounds according to the present invention can temporarily increase the hardness or tension of soft tissue, thereby improving the suturing efficiency during suturing of the soft tissue, thereby preventing aftereffects or the like from occurring due to insufficient anastomosis. In addition, the compounds according to the present invention can temporarily increase the hardness or tension of soft tissue, particularly pancreas, thereby increasing the suturing efficiency during pancreaticoduodenectomy and effectively preventing pancreatic leakage.
• Acyloxymethyl as a drug protecting group. Part 7: Tertiary sulfonamidomethyl ester prodrugs of benzylpenicillin: chemical hydrolysis and anti-bacterial activity
  作者：Jim Iley、Helena Barroso、Rui Moreira、Francisca Lopes、Teresa Calheiros

  DOI：10.1016/s0968-0896(00)00099-7

  日期：2000.7

  are the ultimate products detected and isolated, indicating that beta-lactam ring opening is much slower than ester hydrolysis. As expected from the high reactivity, benzylpenicillin esters (4) displayed similar in vitro antibacterial activity to benzylpenicillin itself. Compared to the benzylpenicillin derivatives, sulfonamidomethyl esters of benzoic, clofibric and valproic acids display a much higher

  合成了苄青霉素（4）的叔磺酰胺基甲基酯，并将其评估为β-内酰胺抗生素的一类新的潜在前药。用HPLC研究了它们在水性缓冲液中的水解，并揭示了一个U形pH速率分布图，其pH依赖性过程从ca开始延伸。pH 2至 pH10。该途径的特征在于动力学数据，该动力学数据与涉及限速亚胺离子形成和青霉素排出的单分子机理相符。苄青霉素和相应的磺酰胺是检测和分离出的最终产物，表明β-内酰胺开环比酯水解慢得多。如从高反应性所期望的，苄青霉素酯（4）在体外具有与苄青霉素本身相似的抗菌活性。与苄青霉素衍生物相比，