3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one | 471294-85-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one
• CAS: 471294-85-6
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: XWMLUXDVMHHLRG-UHFFFAOYSA-N

物化性质

• 沸点：
  529.4±50.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one 在 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 (R)-2-Amino-N-{2-methoxy-5-[3-oxo-2-(3,4,5-trimethoxy-phenyl)-cyclopent-1-enyl]-phenyl}-propionamide; hydrochloride
  参考文献：
  名称：

  Water soluble prodrugs of the antitumor agent 3-[(3-amino-4-methoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)cyclopent-2-ene-1-one

  摘要：

  Fourteen prodrugs of the antitumor agent 3-[(3-amino-4-methoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)cyclopent-2-ene-1-one (1) were prepared to improve its water solubility and potency. These prodrugs include alpha-amino acid (1a-1h), aliphatic amino acid (1i-1I), phosphoramidate (1m), and phosphate (1n) derivatives. All of the prodrugs showed improved water solubility. A number of the amino acid prodrugs (1a, 1b, 1d-1f, 1h, 1j, and 1k) exhibited more potent antitumor activity compared to the parent compound (1). The phosphate prodrug In also offered a potent antitumor activity, but the phosphoramidate 1m did not show any antitumor activity in vivo. None of the prodrugs exhibited significant toxicities in mice. These results indicate that the design and preparation of the amino acid prodrugs (1a, 1b, 1d-1f, 1h, 1j, and 1k) and phosphate prodrug (1n) are beneficial for enhancing the antitumor activity of 1. The similar approaches may be used to improve water solubility and bioactivity of other poorly soluble aromatic amines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00514-x
• 作为产物：
  描述：

  3,4,5-trimethoxyphenylacetyl chloride 在 吡啶 、 TEA 、 硫酸 、 溶剂黄146 、 magnesium bromide 、 锌 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 9.5h， 生成 3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one
  参考文献：
  名称：

  Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues

  摘要：

  A series of 2-(3,4,5-trimethoxyphenyl)-3-arylcyclopent-2-ene-1-ones (8a-8e) and their related analogues, including pentenone 9a, pentenol 10a, pentene 12a, and furane 15, were synthesized and evaluated for cytotoxicity against murine and human tumor cell lines. Compounds 8a-c, 8e and 9a showed strong cytotoxicity with IC50 values in the range of 8-34 ng/mL. Compound 8e exhibited significant anti-tumor activity in BDF1 mice bearing Lewis lung carcinoma cells with an inhibition ratio of 59%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00321-9

文献信息

• PROCESS OF PREPARATION OF DELTA-9-THC-AMINO ACID ESTERS
  申请人：University of Mississippi

  公开号：EP2352497B1

  公开（公告）日：2017-02-22
• COMPOSITIONS CONTAINING DELTA-9-THC-AMINO ACID ESTERS AND PROCESS OF PREPARATION
  申请人：Elsohly Mahmoud A.

  公开号：US20110275555A1

  公开（公告）日：2011-11-10

  Compositions of the formulae (I), (II) and (III); where R1, R2 and R3 are residues of amino acids such as, but not limited to, valine, sarcosine, leucine, glutamine, tryptophan, tyrosine, alanine and 4(4-aminophenyl)butyric acid or combination thereof, and salts thereof. Methods of preparation of these compositions and methods of treating any disease condition responsive to THC comprising administration of at least one these compositions in a pharmaceutically acceptable carrier using a pharmaceutically acceptable formulation.
• US8809261B2
  申请人：——

  公开号：US8809261B2

  公开（公告）日：2014-08-19
• Water soluble prodrugs of the antitumor agent 3-[(3-amino-4-methoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)cyclopent-2-ene-1-one
  作者：Nguyen-Hai Nam、Yong Kim、Young-Jae You、Dong-Ho Hong、Hwan-Mook Kim、Byung-Zun Ahn

  DOI：10.1016/s0968-0896(02)00514-x

  日期：2003.3

  Fourteen prodrugs of the antitumor agent 3-[(3-amino-4-methoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)cyclopent-2-ene-1-one (1) were prepared to improve its water solubility and potency. These prodrugs include alpha-amino acid (1a-1h), aliphatic amino acid (1i-1I), phosphoramidate (1m), and phosphate (1n) derivatives. All of the prodrugs showed improved water solubility. A number of the amino acid prodrugs (1a, 1b, 1d-1f, 1h, 1j, and 1k) exhibited more potent antitumor activity compared to the parent compound (1). The phosphate prodrug In also offered a potent antitumor activity, but the phosphoramidate 1m did not show any antitumor activity in vivo. None of the prodrugs exhibited significant toxicities in mice. These results indicate that the design and preparation of the amino acid prodrugs (1a, 1b, 1d-1f, 1h, 1j, and 1k) and phosphate prodrug (1n) are beneficial for enhancing the antitumor activity of 1. The similar approaches may be used to improve water solubility and bioactivity of other poorly soluble aromatic amines. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues
  作者：Nguyen-Hai Nam、Yong Kim、Young-Jae You、Dong-Ho Hong、Hwan-Mook Kim、Byung-Zun Ahn

  DOI：10.1016/s0960-894x(02)00321-9

  日期：2002.8

  A series of 2-(3,4,5-trimethoxyphenyl)-3-arylcyclopent-2-ene-1-ones (8a-8e) and their related analogues, including pentenone 9a, pentenol 10a, pentene 12a, and furane 15, were synthesized and evaluated for cytotoxicity against murine and human tumor cell lines. Compounds 8a-c, 8e and 9a showed strong cytotoxicity with IC50 values in the range of 8-34 ng/mL. Compound 8e exhibited significant anti-tumor activity in BDF1 mice bearing Lewis lung carcinoma cells with an inhibition ratio of 59%. (C) 2002 Elsevier Science Ltd. All rights reserved.