7-[[2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 121123-17-9

• 物质功能分类: 原料药 - 抗生素类药物 - β-内酰胺酶抑制剂
• 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: 7-[[2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 121123-17-9
• 化学式: C₁₈H₁₉N₃O₅S
• 分子量: 389.4
• InChiKey: WDLWHQDACQUCJR-IHWYPQMZSA-N

物化性质

• 熔点：
  >194°C (dec.)
• 溶解度：
  微溶于水和甲醇，几乎不溶于丙酮。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S26,S36/37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29419000,2941905990

制备方法与用途

根据提供的信息,可以总结出头孢丙烯的制备过程如下:

1. 以碘代苯乙酮为原料,经碘化、偶联反应得到化合物III。

2. 化合物III与3-苯氧基-4-(1H-四唑-5-基)苯甲酸在氯仿中偶联,得到化合物IV。

3. 头孢丙烯粗品通过三氟乙酸处理,再经制备HPLC纯化得到头孢丙烯纯品。

4. 纯化后的头孢丙烯收率为约40%左右。

5. 最终产品为白色棱状结晶,熔点218-220℃(分解)。

6. 制备过程中涉及的主要步骤包括:碘代反应、偶联反应、有机溶剂处理、酸处理、层析纯化等。

7. 主要原料有碘代苯乙酮和3-苯氧基-4-(1H-四唑-5-基)苯甲酸。

8. 总的来说,该合成路线相对复杂,需要多个步骤才能得到最终产品。

文献信息

• New derivatives of cephalosporin for treating cancer
  申请人：Institut Curie

  公开号：EP2926815A1

  公开（公告）日：2015-10-07

  The present invention relates to a new class of cephalosporin derivatives of formula (I), notably having CXCR4 receptor antagonist effect, useful as a therapeutic agent for treating cancer, in particular for treating breast cancer, lung cancer and uveal melanoma. The invention further relates to a pharmaceutical composition comprising a compound of formula (I) and an additional antitumor drug for treating cancer.

  本发明涉及一类新的式(I)头孢菌素衍生物，特别是具有 CXCR4 受体拮抗剂作用的衍生物，可作为治疗癌症，特别是治疗乳腺癌、肺癌和葡萄膜黑色素瘤的治疗剂。本发明还涉及一种药物组合物，该药物组合物包含式（I）化合物和另一种治疗癌症的抗肿瘤药物。
• Derivatives of cephalosporin for treating cancer
  申请人：INSTITUT CURIE

  公开号：US10821114B2

  公开（公告）日：2020-11-03

  The present invention relates to a new class of cephalosporin derivatives of formula (I), notably having CXCR4 receptor antagonist effect, useful as a therapeutic agent for treating cancer, in particular for treating breast cancer, lung cancer and uveal melanoma. The invention further relates to a pharmaceutical composition comprising a compound of formula (I) and an additional antitumor drug for treating cancer.

  本发明涉及一类新的式(I)头孢菌素衍生物，特别是具有 CXCR4 受体拮抗剂作用的衍生物，可作为治疗癌症，特别是治疗乳腺癌、肺癌和葡萄膜黑色素瘤的治疗剂。本发明还涉及一种药物组合物，该药物组合物包含式（I）化合物和另一种治疗癌症的抗肿瘤药物。
• DERIVATIVES OF CEPHALOSPORIN FOR TREATING CANCER
  申请人：Institut Curie

  公开号：EP3125901B1

  公开（公告）日：2018-06-06
• Therapy for Treating Resistant Bacterial Infections
  申请人：Patel Mahesh Vithalbhai

  公开号：US20090275552A1

  公开（公告）日：2009-11-05

  The invention relates to an improved therapy for treating resistant bacterial infections caused by extended-spectrum β-lactamase (ESBLs)-producing strains in a warm-blooded animal, adjuvant step down therapy, and pharmaceutical compositions for such therapies. The invention also relates to a method for inhibiting bacterial resistance in ESBLs-producing strains so as to have better control over the therapy; achieve reduced hospital stay and adjuvant step down therapy so as to avoid recrudescence. In particular, the therapy includes antibacterial combination of cefepime with sulbactam via parenteral route, followed by oral third generation cephalosporin with a suitable β lactamase inhibitor.
• NEW DERIVATIVES OF CEPHALOSPORIN FOR TREATING CANCER
  申请人：INSTITUT CURIE

  公开号：US20170119784A1

  公开（公告）日：2017-05-04

  The present invention relates to a new class of cephalosporin derivatives of formula (I), notably having CXCR4 receptor antagonist effect, useful as a therapeutic agent for treating cancer, in particular for treating breast cancer, lung cancer and uveal melanoma. The invention further relates to a pharmaceutical composition comprising a compound of formula (I) and an additional antitumor drug for treating cancer.