Carbonic acid 4-((S)-2-{(S)-2-[6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-hexanoylamino]-3-phenyl-propionylamino}-6-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-hexanoylamino)-benzyl ester 4-nitro-phenyl ester | 159857-66-6

• 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: Carbonic acid 4-((S)-2-{(S)-2-[6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-hexanoylamino]-3-phenyl-propionylamino}-6-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-hexanoylamino)-benzyl ester 4-nitro-phenyl ester
• 英文别名: (2S)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-phenylpropanoyl]amino]-6-[[(4-methoxyphenyl)-diphenylmethyl]azaniumyl]-N-[4-[(4-nitrophenoxy)carbonyloxymethyl]phenyl]hexanimidate
• CAS: 159857-66-6
• 化学式: C₅₉H₆₀N₆O₁₁
• 分子量: 1029.16
• InChiKey: LDOYBHPKVGFNCE-XWQGWOARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  76
• 可旋转键数：
  28
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  227
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  盐酸多柔比星 、 Carbonic acid 4-((S)-2-{(S)-2-[6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-hexanoylamino]-3-phenyl-propionylamino}-6-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-hexanoylamino)-benzyl ester 4-nitro-phenyl ester 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以66%的产率得到
  参考文献：
  名称：

  Monomethoxytrityl (MMT) as a versatile amino protecting group for complex prodrugs of anticancer compounds sensitive to strong acids, bases and nucleophiles

  摘要：

  Cathepsin B-sensitive maleimidocaproyl-Phe-Lys linker compounds containing acid-sensitive anticancer drugs doxorubicin, mitomycin C and paclitaxel (taxol(R)) attached through a self-immolative p-aminobenzylcarbonyl spacer were prepared using monomethoxytrityl (MMT) as the amino protecting group for Lys. MMT could be removed cleanly and in high yield by dichloroacetic and chloroacetic acids in the presence of anisole with minimal workup. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01158-1
• 作为产物：
  描述：

  (S)-2-((((9h-芴-9-基)甲氧基)羰基)氨基)-6-(((4-甲氧基苯基)二苯基甲基)氨基)己酸 在 lithium hydroxide 、 molecular sieve 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 Carbonic acid 4-((S)-2-{(S)-2-[6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-hexanoylamino]-3-phenyl-propionylamino}-6-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-hexanoylamino)-benzyl ester 4-nitro-phenyl ester
  参考文献：
  名称：

  Monomethoxytrityl (MMT) as a versatile amino protecting group for complex prodrugs of anticancer compounds sensitive to strong acids, bases and nucleophiles

  摘要：

  Cathepsin B-sensitive maleimidocaproyl-Phe-Lys linker compounds containing acid-sensitive anticancer drugs doxorubicin, mitomycin C and paclitaxel (taxol(R)) attached through a self-immolative p-aminobenzylcarbonyl spacer were prepared using monomethoxytrityl (MMT) as the amino protecting group for Lys. MMT could be removed cleanly and in high yield by dichloroacetic and chloroacetic acids in the presence of anisole with minimal workup. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01158-1

文献信息

• Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
  申请人：Seattle Genetics, Inc.

  公开号：EP2353611A2

  公开（公告）日：2011-08-10

  Drug-Linker-Ligand Conjugates are disclosed in which a Drug is linked to a Ligand via a peptide-based Linker unit. In one embodiment, the Ligand is an Antibody. Drug-Linker compounds and Drug compounds are also disclosed. Methods for treating cancer, an autoimmune disease or an infectious disease using the compounds and compositions of the invention are also disclosed.

  本发明公开了药物-连接体-配体共轭物，其中药物通过基于肽的连接体单元与配体连接。在一个实施方案中，配体是抗体。还公开了药物连接体化合物和药物化合物。还公开了使用本发明化合物和组合物治疗癌症、自身免疫性疾病或传染性疾病的方法。
• Efficient mitomycin C coupling with stable p-nitrophenyl-benzyl carbonates using n-hydroxybenzotriazole as a catalytic additive
  作者：Gene M. Dubowchik、H. Dalton King、Kahnie Pham-Kaplita

  DOI：10.1016/s0040-4039(97)01159-3

  日期：1997.7

  Mitomycin C benzyl carbamates were prepared in high yield from stable p-nitrophenyl carbonates in the presence of catalytic amounts of 1-hydroxybenzotriazole/diisopropylethylamine in DMF. (C) 1997 Elsevier Science Ltd.
• AURISTATIN CONJUGATES AND THEIR USE FOR TREATING CANCER, AN AUTOIMMUNE DISEASE OR AN INFECTIOUS DISEASE
  申请人：Seattle Genetics, Inc.

  公开号：EP1545613B1

  公开（公告）日：2011-07-20
• DRUG CONJUGATES AND THEIR USE FOR TREATING CANCER, AN AUTOIMMUNE DISEASE OR AN INFECTIOUS DISEASE
  申请人：Senter Peter D.

  公开号：US20100062008A1

  公开（公告）日：2010-03-11

  Drug-Linker-Ligand Conjugates are disclosed in which a Drug is linked to a Ligand via a peptide-based Linker unit. In one embodiment, the Ligand is an Antibody. Drug-Linker compounds and Drug compounds are also disclosed. Methods for treating cancer, an autoimmune disease or an infectious disease using the compounds and compositions of the invention are also disclosed.
• US7659241B2
  申请人：——

  公开号：US7659241B2

  公开（公告）日：2010-02-09