3-吡啶甲醛,6-(4-甲酰基苯基)- | 98629-44-8

• 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
• 中文名称: 3-吡啶甲醛,6-(4-甲酰基苯基)-
• 英文名称: N-(2-((4-((3-aminopropyl)amino)butyl)amino)-1-methoxy-2-oxoethyl)-7-guanidinoheptanamide
• 英文别名: 11-methoxy-15-deoxyspergualin；N-[4-(3-aminopropyl)aminobutyl]-2-(7-guanidinoheptanamido)-2-methoxyethanamide；1-Amino-19-guanidino-11-methoxy-4,9,12-triazanonadecane-10,13-dione；N-[2-[4-(3-aminopropylamino)butylamino]-1-methoxy-2-oxoethyl]-7-(diaminomethylideneamino)heptanamide
• CAS: 98629-44-8
• 化学式: C₁₈H₃₉N₇O₃
• 分子量: 401.553
• InChiKey: HFNDGMJKLKYYRZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  170
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-吡啶甲醛,6-(4-甲酰基苯基)- 、 环丙甲醛 在 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以34%的产率得到7-Guanidino-heptanoic acid [(4-{[3-(bis-cyclopropylmethyl-amino)-propyl]-cyclopropylmethyl-amino}-butylcarbamoyl)-methoxy-methyl]-amide
  参考文献：
  名称：

  The Long-lasting Antiproliferative Effect of 15-Deoxyspergualin through its Spermidine Moiety.

  摘要：

  15-Deoxyspergualin (DSG) inhibited growth of mouse EL-4 lymphoma cells with an IC50 0.02 μg/ml. Even though the cells were treated with DSG for only 4 hours and then washed, the antiproliferative effect lasted long with an IC50 0.4μg/ml. DSG has spermidine and guanidine moieties in its structure. One decomposed element containing guanidine moiety inhibited the growth at higher doses than DSG, but the effect did not last long unlike DSG. While another element containing spermidine moiety did not affect the growth, it diminished the long-lasting antiproliferative effect of DSG by pretreatment of the cells. Pretreatment with polyamines such as putrescine, spermidine, and spermine also diminished the effect of DSG. Furthermore, N-alkylation of spermidine moiety in DSG abolished the antiproliferative effect. These results suggested that DSG binds to the cells through its spermidine moiety and exerts its long-lasting antiproliferative effect.

  DOI：

  10.7164/antibiotics.53.705
• 作为产物：
  描述：

  庚酸 在 ammonium cerium (IV) nitrate 、 磷酸 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.33h， 生成 3-吡啶甲醛,6-(4-甲酰基苯基)-
  参考文献：
  名称：

  Improved synthesis of 15-deoxyspergualin analogs using the Ugi multi-component reaction

  摘要：

  Spergualin is a natural product that exhibits immunosuppressive, anti-tumor and anti-bacterial activities. Its derivatives, such as 15-deoxyspergualin (15-DSG), have been clinically approved for acute allograft rejection. However, the reported syntheses are cumbersome (>10 steps) and they suffer from low overall yields (similar to 0.3% to 18%). Moreover, spergualin and its derivatives are chemically unstable and rapidly hydrolyzed in aqueous buffer. Here, we have re-explored these issues and report a modified synthetic route with significantly improved overall yield (similar to 31% to 47%). The key transformation is a microwave-accelerated Ugi multi-component reaction that is used to generate the peptoid core in a single step. Using the products of this route, we found that modifications of the hemiaminal significantly increased chemical stability. Thus, we anticipate that this synthetic route will improve access to biologically active 15-DSG derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.079

文献信息

• N-(4-(3-aminopropyl)aminobutyl)-2-(.omega.-gua
  申请人：Bristol-Myers Company

  公开号：US04983328A1

  公开（公告）日：1991-01-08

  N-[4-(3-Aminopropyl)aminobutyl]-2-(.omega.-guanidino-fatty acid-amido)-2-substituted-ethanamides represented by the general formula ##STR1## wherein Y represents --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH or ##STR2## R represents a hydrogen atom, an alkyl group of 1 to 4 carbon atoms which may have a hydroxyl group as substituent, or a benzyl group, and n is an integer of from 1 to 8, provided that when Y is ##STR3## and n is 4, R represents the groups other than the hydrogen atom; salt thereof having antitumor activity in experimental animal tumors and a process for the preparation thereof is provided.

  该文献描述了一种具有抗肿瘤活性的化合物，其化学式为：##STR1## 其中Y代表--CH.sub.2 --CH.sub.2 --、--CH.dbd.CH或##STR2## R代表氢原子、1至4个碳原子的烷基，该烷基可能具有羟基取代基，或苯甲基，n为1至8的整数。当Y为##STR3##且n为4时，R代表除氢原子外的它基团。该文献还提供了一种制备该化合物及其盐的方法。
• N-[4-(3-aminopropyl)-aminobutyl]-2-(.omega.-gua
  申请人：Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

  公开号：US04518532A1

  公开（公告）日：1985-05-21

  N-[4-(3-Aminopropyl)aminobutyl]-2-(.omega.-guanidino-fatty acid-amido)-2-substituted-ethanamides represented by the general formula ##STR1## wherein Y represents --(CH.sub.2 --CH.sub.2 --, --CH.dbd.CH or ##STR2## R represents a hydrogen atom, an alkyl group of 1 to 4 carbon atoms which may have a hydroxyl group as substituent, or a benzyl group, and n is an integer of from 1 to 8, provided that when Y is ##STR3## and n is 4, R represents the groups other than the hydrogen atom; a salt thereof having antitumor activity in experimental animal tumors and a process for the preparation thereof is provided.

  提供一般公式为##STR1##的N-[4-(3-氨基丙基)氨基丁基]-2-(ω-鸟氨酸脂肪酸酰胺)-2-取代乙酰胺，其中Y代表--(CH.sub.2 --CH.sub.2 --，--CH.dbd.CH或##STR2##，R代表氢原子，1至4个碳原子的烷基，可能具有羟基取代物，或苯甲基，n是1至8的整数，但当Y为##STR3##且n为4时，R代表除氢原子以外的基团; 该盐在实验动物肿瘤中具有抗肿瘤活性，提供了其制备方法。
• UMEZAWA, HAMAO;TAKEUCHI, TOMIO;KONDO, SHINICHI;TINUMA, HIRONOBU;IKEDA, DA+
  作者：UMEZAWA, HAMAO、TAKEUCHI, TOMIO、KONDO, SHINICHI、TINUMA, HIRONOBU、IKEDA, DA+

  DOI：——

  日期：——
• UMEHDZAVA, NAMAO;TAKEHUTI, TOMIO;KONDO, SINITI;IINUMA, XIRONOBU;IKEHDA, D+
  作者：UMEHDZAVA, NAMAO、TAKEHUTI, TOMIO、KONDO, SINITI、IINUMA, XIRONOBU、IKEHDA, D+

  DOI：——

  日期：——
• UMEDA, YOSHIHISA;MORIGUCHI, MAKOTO;IKAI, KATSUSHIGE;KURODA, HIROYUKI;NAKA+, J. ANTIBIOTICS, 40,(1987) N 9, 1316-1324
  作者：UMEDA, YOSHIHISA、MORIGUCHI, MAKOTO、IKAI, KATSUSHIGE、KURODA, HIROYUKI、NAKA+

  DOI：——

  日期：——