6-(4'-phenylarsonic acid)aminopurine | 17053-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-(4'-phenylarsonic acid)aminopurine
• 英文别名: N-Purin-6-yl-arsanilsaeure；[4-(9H-purin-6-ylamino)-phenyl]-arsonic acid；Arsonic acid, [4-(1H-purin-6-ylamino)phenyl]-；[4-(7H-purin-6-ylamino)phenyl]arsonic acid
• CAS: 17053-73-5
• 化学式: C₁₁H₁₀AsN₅O₃
• 分子量: 335.154
• InChiKey: HDUWJMRMJBQWKW-UHFFFAOYSA-N

物化性质

• 熔点：
  >300.0 °C
• 沸点：
  602.0±65.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对氨基苯砷酸 、 6-氯嘌呤 在 盐酸 作用下， 以 异丙醇 为溶剂， 以71.3%的产率得到6-(4'-phenylarsonic acid)aminopurine
  参考文献：
  名称：

  具有强抗白血病活性的有机苯基砷酸化合物。

  摘要：

  合成了一系列12种有机砷酸化合物，并针对人B谱系（NALM-6）和T谱系（MOLT-3）急性淋巴细胞白血病（ALL）细胞系进行了评估。铅化合物2-三氯甲基-4- [4'-（4“-苯基偶氮）苯基ar磺酸]氨基喹唑啉（化合物19，PHI-P518; IC（50）=针对NALM-6和2.0 + / 1.1 microM -0.8 microM（针对MOLT-3）和2-甲硫基-4-（2'-苯基砷酸）氨基嘧啶（化合物15，PHI-P381; IC（50）= 1.5 +/- 0.3 microM（针对NALM-6和2.3 + / -0.5 microM（针对MOLT-3）在低微摩尔浓度下表现出强大的抗白血病活性。

  DOI：

  10.1016/s0960-894x(02)00928-9

文献信息

• Uckun, Fatih M.; D'Cruz, Osmond J.; Liu, Xing-Ping, Arzneimittel-Forschung/Drug Research, 2003, vol. 53, # 6, p. 428 - 439
  作者：Uckun, Fatih M.、D'Cruz, Osmond J.、Liu, Xing-Ping、Narla, Rama Krishna

  DOI：——

  日期：——
• Human sperm immobilizing activity of aminophenyl arsenic acid and its N-substituted quinazoline, pyrimidine, and purine derivatives: protective effect of glutathione
  作者：Fatih M. Uckun、Xing-Ping Liu、Osmond J. D’Cruz

  DOI：10.1016/s0890-6238(01)00195-2

  日期：2002.1

  We examined the potential toxicity of pentavalent organic arsenicals for human sperm. We used computer-assisted sperm analysis to examine the effects of three aminophenyl arsenicals and their nine N-substituted quinazoline, pyrimidine, and purine derivatives on human sperm motility and kinematics in human semen and medium. Among the arsenicals examined, (aminophenylazo)-phenyl arsenic acid and its N-substituted pyrimidine derivative PHI-370 (2-methylthio-4-[(4'-aminophenylazo)-phenylarsonic acid] pyrimidine) exhibited rapid sperm immobilizing activity in medium with EC50 values of 77 and 82 muM, respectively, and t(1/2) of <3 min. Molecular modeling analysis indicated that sperm-immobilizing organic arsenicals exhibit high dipole moments (>7 Debyes). Sperm immobilizing activity of these arsenicals was completely abrogated in the presence of seminal plasma. Furthermore, coincubation of motile sperm with PHI-370 in the presence of reduced glutathione (GSH) resulted in dose-dependent protection of sperm motility and sperm motion parameters. Coincubation of the arsenical with GSH at a molar ratio of 1:20 resulted in 95% retention of sperm progressive motility. The mean values of the other sperm movement characteristics also showed >90% protection. These observations suggest that the rapid sperm immobilizing activity of these pentavalent arsenicals may be as a result of direct binding of the arsenical with the sperm thiol components essential for sperm motility as well as induction of oxidative damage by disruption of sperm cell's antioxidant system. Sodium arsanilate and its N-substituted pyrimidine derivative, PHI-370, are useful probes to further evaluate the mechanism of pentavalent arsanilate-induced human sperm dysfunction. (C) 2002 Elsevier Science Inc. All rights reserved.
• Organic phenyl arsonic acid compounds with potent antileukemic activity
  作者：Xing-Ping Liu、Rama Krishna Narla、Fatih M Uckun

  DOI：10.1016/s0960-894x(02)00928-9

  日期：2003.2

  A series of 12 organic arsonic acid compounds has been synthesized and evaluated against human B-lineage (NALM-6) and T-lineage (MOLT-3) acute lymphoblastic leukemia (ALL) cell lines. The lead compounds 2-trichloromethyl-4-[4'-(4"-phenylazo)phenylarsonic acid]aminoquinazoline (compound 19, PHI-P518; IC(50)=1.1+/-0.5 microM against NALM-6 and 2.0+/-0.8 microM against MOLT-3) and 2-methylthio-4-(2'-phenylarsonic

  合成了一系列12种有机砷酸化合物，并针对人B谱系（NALM-6）和T谱系（MOLT-3）急性淋巴细胞白血病（ALL）细胞系进行了评估。铅化合物2-三氯甲基-4- [4'-（4“-苯基偶氮）苯基ar磺酸]氨基喹唑啉（化合物19，PHI-P518; IC（50）=针对NALM-6和2.0 + / 1.1 microM -0.8 microM（针对MOLT-3）和2-甲硫基-4-（2'-苯基砷酸）氨基嘧啶（化合物15，PHI-P381; IC（50）= 1.5 +/- 0.3 microM（针对NALM-6和2.3 + / -0.5 microM（针对MOLT-3）在低微摩尔浓度下表现出强大的抗白血病活性。