porfiromycin | 801-52-5

• 物质功能分类: 生物 - 生物化学试剂 - 抑制剂激活剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: porfiromycin
• 英文别名: N-methylmitomycin C；Methylmitomycin；[(7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
• CAS: 801-52-5
• 化学式: C₁₆H₂₀N₄O₅
• 分子量: 348.359
• InChiKey: HRHKSTOGXBBQCB-FZPCLGDSSA-N

物化性质

• 熔点：
  201.25°C (rough estimate)
• 沸点：
  482.73°C (rough estimate)
• 比旋光度：
  D25 +275 ±55° (c = 0.1% in methanol); D25 +242 ±100° (c = 0.045% in methanol)
• 密度：
  1.1924 (rough estimate)
• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  porfiromycin 在 水 、 sodium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 (6-hydroxy-8a-methoxy-1,5-dimethyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl carbamate
  参考文献：
  名称：

  使用“点击”化学聚合合成甾体抗雌激素-丝裂霉素 C 杂化物†

  摘要：

  基于强效抗增殖药物的结构，开发了一种新型雌激素受体靶向药物杂合体的聚合合成 丝裂霉素C 和甾体抗雌激素 RU 39411。甾体抗雌激素是用叠氮基-三甘醇氧基接头制备的，而丝裂霉素 C 衍生物（卟啉霉素）掺入了一个互补的 7-N 端炔烃。使用 Huisgen [3 + 2] 环加成（“点击”）反应将两种成分连接起来。初步生物学分析表明，最终的杂化化合物保留了有效的抗雌激素和抗增殖活性。

  DOI：

  10.1039/c2ob25902h
• 作为产物：
  描述：

  N-甲基丝裂霉素A 在 ammonium hydroxide 作用下， 生成 porfiromycin
  参考文献：
  名称：

  Stereochemical relationship between mitomycins A, B, and C

  摘要：

  DOI：

  10.1021/jo00208a031

文献信息

• [EN] STEROIDAL ANTI-HORMONE HYBRIDS<br/>[FR] HYBRIDES ANTI-HORMONAUX STÉROÏDIENS
  申请人：UNIV NORTHEASTERN

  公开号：WO2010085747A1

  公开（公告）日：2010-07-29

  Disclosed are novel compounds and compositions for inhibition of androgen and estrogen receptor signaling, methods for inhibiting androgen signaling, methods for inhibiting estrogen signaling, methods for inhibiting the interaction between a co-regulatory protein and an androgen or estrogen receptor, and methods for treating cancer.

  披露了新颖的化合物和组合物，用于抑制雄激素和雌激素受体信号传导，抑制雄激素信号传导的方法，抑制雌激素信号传导的方法，抑制共调节蛋白与雄激素或雌激素受体之间相互作用的方法，以及治疗癌症的方法。
• A systematic study on the chemical stability of mitomycin A and mitomycin B.
  作者：Jos H. BEIJNEN、OEDS A.G.J. VAN DER HOUWEN、HILDE ROSING、WILLY J.M. UNDERBERG

  DOI：10.1248/cpb.34.2900

  日期：——

  The kinetics and mechanisms of the degradation of mitomycin A and mitomycin B in aqueous solution were investigated by means of ultraviolet (UV) spectrophotometry and high-performance liquid chromatography (HPLC). The influences of pH, buffers and temperature on the degradation were quantified. Degradation products were isolated and characterized by mass spectrometry (MS), UV-VIS spectrophotometry, chromatography and circular dirchroism (CD) spetroscopy. The degradation reactions follow (pseudo) first-order kinetics. The collected kinetic data allowed an accurate determination of the pKa value of the aziridine moiety of the mitomycins by using computerized curve-fitting models.

  通过紫外（UV）分光光度法和高性能液相色谱（HPLC）研究了丝裂霉素A和丝裂霉素B在水溶液中的降解动力学和机理。定量分析了pH值、缓冲液和温度对降解的影响。通过质谱（MS）、紫外-可见分光光度法、色谱法和圆二色谱（CD）光谱法分离和鉴定了降解产物。降解反应遵循（准）一级动力学。收集的动力学数据通过计算机化曲线拟合模型准确测定了丝裂霉素中氮丙啶部分的pKa值。
• Solvolysis Study of Cycliciminomitomycins
  作者：Younghwa Na

  DOI：10.1248/cpb.55.482

  日期：——

  The solvolysis rates for the substituted C(7)-cyclohexylamino- or C(8)-cyclohexyliminomitomycins 8-19 were determined in buffered methanolic solutions (0.06 M bis-Tris·HCl, pH: 5.5) at 25 °C and then compared with mitomycin C (1) and porfiromycin. Kinetic studies showed that C(8)-cyclohexyliminomitomycins 8-13 underwent solvolysis 150-230 times faster than mitomycin C (1) to give C(1)-methoxymitosene products. The solvolysis rates were slightly faster than that reported for 6. The C(7)-(2′-hydroxy)cyclohexylaminomitomycins 16-19 exhibited comparable solvolysis rates with 1 and porfiromycin.

  取代的 C(7)-环己基氨基-或 C(8)-环己基亚氨基丝裂霉素 8-19 的溶剂分解率在缓冲甲醇溶液（0.06 M bis-Tris·HCl，pH：5.5）中测定。 25 °C，然后与丝裂霉素 C (1) 和卟啉霉素进行比较。动力学研究表明，C(8)-环己基亚氨基丝裂霉素8-13的溶剂分解速度比丝裂霉素C(1)快150-230倍，产生C(1)-甲氧基丝裂霉素产物。溶剂分解速率比报道的 6 稍快。C(7)-(2'-羟基)环己基氨基丝裂霉素 16-19 表现出与 1 和卟啉霉素相当的溶剂分解速率。
• Hong; Kohn, Harold, Journal of the American Chemical Society, 1991, vol. 113, # 12, p. 4634 - 4644
  作者：Hong、Kohn, Harold

  DOI：——

  日期：——
• 7-Aminoaziridinomitosenes: synthesis, structure, and chemistry
  作者：Insook Han、Harold Kohn

  DOI：10.1021/jo00015a016

  日期：1991.7

  7-Aminoleucoaziridinomitosene (2a) has been proposed as a key intermediate in the reductive activation process for the antineoplastic agent, mitomycin C (1a). Little is known about 2a and its oxidized equivalent, 7-aminoaziridinomitosene (3a). An expedient electrochemical procedure for 3a and the corresponding N-methyl analogue 3b has been developed. NMR spectral studies of 3a in DMF-d7 and DMSO-d6 provided important information concerning the solution-state structure for this adduct. Factors controlling the aziridine ring-opening process under reductive and nonreductive conditions have been determined, as well as evidence for the intermediacy of 2a in the reductive activation cascade of 1a.