N-[5-({[5-({[2-(carbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide | 17165-05-8

• 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: N-[5-({[5-({[2-(carbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide
• 英文别名: β-(1-Methyl-4-<1-methyl-4-(1-methyl-4-formamido-pyrrol-2-carbonamido)-pyrrol-2-carbonamido>-pyrrol-2-carbonamido)-propionamid；N-[5-[[5-[(3-amino-3-oxopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide
• CAS: 17165-05-8
• 化学式: C₂₂H₂₆N₈O₅
• 分子量: 482.499
• InChiKey: GTWPGXOOWBQOEK-UHFFFAOYSA-N

物化性质

• 熔点：
  187-189 °C
• 沸点：
  749.0±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  174
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[5-({[5-({[2-(carbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide 在 盐酸 、 TEA 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 N-[5-({[5-({[2-(carbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-[N,N-bis(oxiranylmethyl)amino]-1-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Design, Synthesis and Growth Inhibition Activity of Bis-Epoxyethyl Derivatives of Stallimycin Modified on the Amidino Moiety

  摘要：

  Derivatives 3-6 of stallimycin (distamycin A) rnodified a t the C-terminal amidine moiety and tethered to a bis-epoxyethyl moiety (as DNA alkylating unit) at the N-terminal position have been prepared and tested for in vitro cytotoxic activity against two different leukemik cell lines, K562 and L1210. None of the compounds without epoxide was active. A comparison of the biological activity related to the diepoxy compounds 3-6 with different non-basic amidine modified moieties, showed low activity for the carbamoyl and N-methyl carbamoyl derivatives (compounds 5 and 6, respectively), moderate activity for the amidoxime analogue 4, good activity for the cyanamidine derivative 3.

  DOI：

  10.1007/s00044-004-0034-6
• 作为产物：
  描述：

  偏端霉素A盐酸盐 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 生成 N-[5-({[5-({[2-(carbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Cytotoxic α-bromoacrylic derivatives of distamycin analogues modified at the amidino moiety

  摘要：

  The design, synthesis, in vitro and in vivo activities of novel alpha-bromoacrylic derivatives of distamycin A, modified at the amidino moiety by the replacement with basic or non-basic groups are reported. In spite of the relevance of these modifications of distamycin frame, the new derivatives are potent cytotoxics. The presence of the amidino moiety, is, therefore, not an absolute requirement for the activity. In particular due to a favorable myclotoxicity/cytotoxicity ratio, guanidino derivative PNU 166196 was selected for clinical development. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00205-5

文献信息

• Acryloyl substituted distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents
  申请人：Pharmacia & Upjohn S.p.A.

  公开号：US20030023031A1

  公开（公告）日：2003-01-30

  According to the invention, there is provided a method of manufacturing a medicament for use in the treatment of cancer or viral infections which comprises obtaining a cancer treating effective amount of a compound of formula (I), 1 and combining the compound of formula (I) with at least one pharmaceutically acceptable excipient, and wherein the cancer treating effective amount of a compound of formula I is an acryloyl substituted distamycin derivative in which n, R 1 and R 2 , R 3 , B, are defined herein or a pharmaceutically acceptable salt thereof to produce a medicament for use in the treatment of cancer or viral infections.

  根据本发明，提供了一种制造治疗癌症或病毒感染的药物的方法，该方法包括获取公式（I）化合物的治疗癌症有效量，1并将公式（I）化合物与至少一种药用可接受的赋形剂结合，其中公式I化合物的治疗癌症有效量是一种丙烯酰基取代的二氨基链霉素衍生物，其中n，R1和R2，R3，B在此定义，或其药用可接受盐，以制备用于治疗癌症或病毒感染的药物。
• ACRYLOYL SUBSTITUTED DISTAMYCIN DERIVATIVES, PROCESS FOR PREPARING THEM, AND THEIR USE AS ANTITUMOR AND ANTIVIRAL AGENTS
  申请人：PHARMACIA & UPJOHN S.p.A.

  公开号：EP0915845B1

  公开（公告）日：2001-09-12
• NEW ALKYLATING AGENTS
  申请人：Nerviano Medical Sciences S.r.l.

  公开号：EP2836494B1

  公开（公告）日：2019-08-21
• US6165980A
  申请人：——

  公开号：US6165980A

  公开（公告）日：2000-12-26
• Cytotoxic α-bromoacrylic derivatives of distamycin analogues modified at the amidino moiety
  作者：Paolo Cozzi、Italo Beria、Marina Caldarelli、Cristina Geroni、Nicola Mongelli、Giulia Pennella

  DOI：10.1016/s0960-894x(00)00205-5

  日期：2000.6

  The design, synthesis, in vitro and in vivo activities of novel alpha-bromoacrylic derivatives of distamycin A, modified at the amidino moiety by the replacement with basic or non-basic groups are reported. In spite of the relevance of these modifications of distamycin frame, the new derivatives are potent cytotoxics. The presence of the amidino moiety, is, therefore, not an absolute requirement for the activity. In particular due to a favorable myclotoxicity/cytotoxicity ratio, guanidino derivative PNU 166196 was selected for clinical development. (C) 2000 Elsevier Science Ltd. All rights reserved.