(3S, 6R)-3-aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one | 270902-70-0

• 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: (3S, 6R)-3-aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one
• 英文别名: [(3R,6S)-6-amino-7-oxoazepan-3-yl] cyclohexanecarboxylate
• CAS: 270902-70-0
• 化学式: C₁₃H₂₂N₂O₃
• 分子量: 254.329
• InChiKey: NIFLAEPGYWFNBP-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S, 6R)-3-aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one 在 三氟乙酸 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 24.5h， 生成 (2R,3R,4S,5R,6E)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-N-[(3S,6R)-hexahydro-2-oxo-6-(cyclohexylcarbonyl)oxy-2H-azepin-3-yl]non-6-enamide
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Ester-Modified Analogues of Bengamide B

  摘要：

  Bengamide B, a novel sponge-derived marine natural product with broad spectrum antitumor activity, was not suitable for further preclinical development because of its difficult synthesis and very poor water solubility. Bengamide B produced a 31% T/C at its solubility-limited maximum intravenous dose of 33 micromol/kg in MDA-MB-435 breast carcinoma implanted subcutaneously as a xenograft in nude mice. Compound 8a, a bengamide B analogue with three structural changes (t-Bu alkene substituent, unsubstituted lactam nitrogen, and inverted lactam 5'-myristoyloxy group), was as potent as bengamide B in vitro and more efficacious than bengamide B in vivo. A series of ester-modified analogues based on 8a were synthesized and tested in vitro and in vivo (MDA-MB-435). The cyclohexyl- and phenethyl-substituted esters, 8c and 8g, respectively, had in vitro and in vivo activities similar to that of 8a and enhanced water solubility (ca. 1 mg/mL). Consequently, 8c and 8g were tested in the MDA-MB-435 xenograft model at 100 micromol/kg and produced 29% and 57% tumor regression, respectively.

  DOI：

  10.1021/jm010188c
• 作为产物：
  描述：

  (3S,6R)-3-(tert-butyloxycarbonyl)aminohexahydro-6-hydroxy-2H-azepin-2-one 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3S, 6R)-3-aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Ester-Modified Analogues of Bengamide B

  摘要：

  Bengamide B, a novel sponge-derived marine natural product with broad spectrum antitumor activity, was not suitable for further preclinical development because of its difficult synthesis and very poor water solubility. Bengamide B produced a 31% T/C at its solubility-limited maximum intravenous dose of 33 micromol/kg in MDA-MB-435 breast carcinoma implanted subcutaneously as a xenograft in nude mice. Compound 8a, a bengamide B analogue with three structural changes (t-Bu alkene substituent, unsubstituted lactam nitrogen, and inverted lactam 5'-myristoyloxy group), was as potent as bengamide B in vitro and more efficacious than bengamide B in vivo. A series of ester-modified analogues based on 8a were synthesized and tested in vitro and in vivo (MDA-MB-435). The cyclohexyl- and phenethyl-substituted esters, 8c and 8g, respectively, had in vitro and in vivo activities similar to that of 8a and enhanced water solubility (ca. 1 mg/mL). Consequently, 8c and 8g were tested in the MDA-MB-435 xenograft model at 100 micromol/kg and produced 29% and 57% tumor regression, respectively.

  DOI：

  10.1021/jm010188c

文献信息

• Certain substituted caprolactams, pharmaceutical compositions containing them and a process for their preparation
  申请人：Novartis AG

  公开号：US06239127B1

  公开（公告）日：2001-05-29

  The present invention relates to certain substituted caprolactam compounds of formula (I), where R1 is (C1-6)alkyl or (C3-6)cycloalkyl; R2 hydrogen or (C1-6)alkyl; X is (C1-12)alkynylene; (C2-12)alkynylene; m is 0 or 1; and R3 is (C3-8)cycloalkyl; or an aromatic ring system selected from (II, III, IV and V), where R4 is hydrogen, chloro, or methoxy; R5 is hydrogen, chloro, (C1-18)alkyl or (C1-18)alkoxy, and Z is oxygen, sulfur, N—H, or N—CH3; or a pharmaceutically acceptable acid addition salt thereof, where possible, pharmaceutical compositions containing said compounds, the use of said compounds in treating tumors and to a process for making said compounds.

  本发明涉及一些式子为(I)的取代己内酰胺化合物，其中R1是（C1-6）烷基或（C3-6）环烷基；R2是氢或（C1-6）烷基；X是（C1-12）炔基；（C2-12）炔基；m为0或1；而R3是（C3-8）环烷基；或从（II，III，IV和V）中选择的芳香环系统，其中R4是氢，氯或甲氧基；R5是氢，氯，（C1-18）烷基或（C1-18）烷氧基，而Z是氧，硫，N-H或N-CH3；或其药学上可接受的酸盐，如有可能，含有该化合物的药物组合物，以及使用该化合物治疗肿瘤的方法和制备该化合物的过程。
• Use of certain substituted caprolactams in treating tumors
  申请人：——

  公开号：US20010044433A1

  公开（公告）日：2001-11-22

  The present invention relates to certain substituted caprolactam compounds, pharmaceutical compositions containing said compounds, the use of said compounds in treating tumors and to a process for making said compounds.

  本发明涉及某些取代的己内酰胺化合物、含有该化合物的药物组合物、使用该化合物治疗肿瘤的方法以及制备该化合物的过程。
• CERTAIN SUBSTITUTED CAPROLACTAMS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USE IN TREATING TUMORS
  申请人：Novartis AG

  公开号：EP1131297B1

  公开（公告）日：2004-04-14