3-amino-5-hydroxybenzyl alcohol | 771437-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-amino-5-hydroxybenzyl alcohol
• 英文别名: 3-Amino-5-(hydroxymethyl)phenol
• CAS: 771437-32-2
• 化学式: C₇H₉NO₂
• mdl: MFCD19204791
• 分子量: 139.154
• InChiKey: KWXWLBSPCCKZKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-5-hydroxybenzyl alcohol 在 盐酸 、 potassium fluoride 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3-(acridin-9-ylamino)-5-{2-[bis(2-chloroethyl)amino]ethoxy}phenyl)methanol
  参考文献：
  名称：

  Potent antitumor N-mustard derivatives of 9-anilinoacridine, synthesis and antitumor evaluation

  摘要：

  A series of 9-anilinoacridine N-mustard derivatives, in which the alkylating N-mustard residue was linked to the C-3' or C-4' position of the anilino ring with an O-ethylene spacer, was synthesized and evaluated for cytotoxicity against human lymphoblastic leukemic cells (CCRF-CEM) in culture. The results showed that all of the new compounds exhibited potent cytotoxicity with IC50 values ranging from 0.002 to 0.7 muM, which were as potent or significantly more potent than 3-(9-acridinylamino)-5-hydroxy-methylaniline (AHMA). Compound 9 did not exhibit cross-resistance against both vinblastine-resistant (CCRF-CEM/VBL) and taxol-resistant (CCRF-CEM/taxol) cells. Additionally, compound 9 demonstrated potent antitumor effect in nude mice bearing human breast carcinoma MX-1 xenografts, resulting in complete tumor remission in two out of three mice at the maximal dose of 1-2 mg/kg (Q3Dx7) or 3 mg/kg (Q4Dx5) via intravenous injection. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.080

文献信息

• 9-anilinoacridine alkylating agents
  申请人：Su Tsann-Long

  公开号：US20080176889A1

  公开（公告）日：2008-07-24

  This invention relates to 9-anilinoacridine alkylating agents, their synthesis and their use in pharmaceutical compositions for treating diseases.

  这项发明涉及9-苯胺基吖啶烷基化剂，它们的合成以及它们在治疗疾病的药物组合物中的应用。
• Potent antitumor 9-anilinoacridines bearing an alkylating N-mustard residue on the anilino ring: synthesis and biological activity
  作者：Valeriy A. Bacherikov、Ting-Chao Chou、Hua-Jin Dong、Xiuguo Zhang、Ching-Huang Chen、Yi-Wen Lin、Tsong-Jen Tsai、Rong-Zau Lee、Leroy F. Liu、Tsann-Long Su

  DOI：10.1016/j.bmc.2005.03.057

  日期：2005.6

  A series of N-mustard derivatives of 9-anilinoacridine was synthesized for antitumor and structure-activity relationship studies. The alkylating N-mustard residue was linked to the C-3' or C-4' position of the anilino ring with an O-ethylene (O-C-2) O-butylene (O-C-4), and methylene (C-1) spacer. All of the new N-mustard derivatives exhibited significant cytotoxicity in inhibiting human lymphoblastic leukemic cells (CCRF-CEM) in culture. Of these agents, (3-(acridin-9-ylamino)-5-2-[bis(2-chloroethyl)amino]ethoxy}phenyl)methanol (10) was subjected to antitumor studies, resulting in an approximately 100-fold more potent effect than its parent analogue 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA) in inhibiting the growth of human lymphoblastic leukemic cells (CCRF-CEM) in vitro. This agent did not exhibit cross-resistance against vinblastine-resistant (CCRF-CEM/VBL) or Taxol-resistant (CCRF-CEM/Taxol) cells. Remarkably, the therapeutic effect of 10 at a dose as low as one tenth of the Taxol therapeutic dose [i.e., 1-2 mg/kg (Q3D x 7) or 3 mg/kg (Q4D x 5); intravenous injection] on nude mice bearing human breast carcinoma MX-1 xenografts resulted in complete tumor remission in two out of three mice. Furthermore, 10 yielded xenograft tumor suppression of 81-96% using human T-cell acute lymphoblastic leukemia CCRF-CEM, colon carcinoma HCT-116, and ovarian adenocarcinoma SK-OV-3 tumor models. (c) 2005 Elsevier Ltd. All rights reserved.
• Potent Antitumor 9-Anilinoacridines and Acridines Bearing an Alkylating <i>N</i>-Mustard Residue on the Acridine Chromophore:  Synthesis and Biological Activity
  作者：Tsann-Long Su、Yi-Wen Lin、Ting-Chao Chou、Xiuguo Zhang、Valeriy A. Bacherikov、Ching-Huang Chen、Leroy F. Liu、Tsong-Jen Tsai

  DOI：10.1021/jm060197r

  日期：2006.6.1

  A series of 9-anilinoacridine and acridine derivatives bearing an alkylating N-mustard residue at C4 of the acridine chromophore were synthesized. The N-mustard pharmacophore was linked to the C4 of the acridine ring with an O-ethyl ( O-C-2), O-propyl ( O-C-3), or O-butyl ( O-C-4) spacer. It revealed that all newly synthesized compounds were very potent cytotoxic agents against human leukemia and various solid tumors in vitro. These agents did not exhibit cross-resistance against vinblastine-resistant ( CCRF-CEM/VBL) or taxol-resistant ( CCRF-CEM/taxol) cells. It also showed that these agents were DNA cross-linking agents rather than topoisomerase II inhibitors. Of these agents, compounds 27a and 27c were shown to have potent antitumor activity in nude mice bearing the human breast carcinoma MX-1 xenograft. The therapeutic efficacies of these two agents are comparable to that of taxol.
• NOVEL SURFACE ACTIVE POLYMERIC-DENDRON SYSTEMS
  申请人：UNIVERSITY OF DURHAM

  公开号：EP1907452B1

  公开（公告）日：2017-04-05