3-methoxyglutaraldehyde | 79867-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxyglutaraldehyde
• 英文别名: 3-Methoxypentanedial
• CAS: 79867-82-6
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: YXXJIBOFQVPSDA-UHFFFAOYSA-N

物化性质

• 沸点：
  229.6±20.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  柔红霉素 盐酸盐 、 3-methoxyglutaraldehyde 在 sodium cyanoborohydride 作用下， 生成 (7S,9S)-6,9,11-trihydroxy-9-(1-hydroxyethyl)-7-[(2R,4S,5S,6S)-5-hydroxy-4-(4-methoxypiperidin-1-yl)-6-methyloxan-2-yl]oxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione 、 MeO
  参考文献：
  名称：

  Enhanced antitumor properties of 3'-(4-morpholinyl) and 3'-(4-methoxy-1-piperidinyl) derivatives of 3'-deaminodaunorubicin

  摘要：

  Reductive N,N-dialkylation of daunorubicin with 2,2'-oxydiacetaldehyde and NaBH3CN occurred in two steps without interruption and with cyclization to form 3'-(4-morpholinyl)-3'-deaminodaunorubicin. This derivative retained the antitumor efficacy of doxorubicin against mouse leukemia P388 but at one-fortieth the dose; hence, it is the most potent anthracycline analogue synthesized so far. The 4-methoxy-1-piperidinyl derivative, similarly prepared with 3-methoxyglutaraldehyde, showed improved efficacy against P388, though at normal doses. Results with a series of analogues indicate that incorporation of the N in the new ring and the presence of an ether O at the 4-position are critical for enhanced activity.

  DOI：

  10.1021/jm00343a004
• 作为产物：
  描述：

  1,2-dihydroxy-4-methoxycyclopentane 在 sodium periodate 作用下， 以 水 为溶剂， 生成 3-methoxyglutaraldehyde
  参考文献：
  名称：

  Enhanced antitumor properties of 3'-(4-morpholinyl) and 3'-(4-methoxy-1-piperidinyl) derivatives of 3'-deaminodaunorubicin

  摘要：

  Reductive N,N-dialkylation of daunorubicin with 2,2'-oxydiacetaldehyde and NaBH3CN occurred in two steps without interruption and with cyclization to form 3'-(4-morpholinyl)-3'-deaminodaunorubicin. This derivative retained the antitumor efficacy of doxorubicin against mouse leukemia P388 but at one-fortieth the dose; hence, it is the most potent anthracycline analogue synthesized so far. The 4-methoxy-1-piperidinyl derivative, similarly prepared with 3-methoxyglutaraldehyde, showed improved efficacy against P388, though at normal doses. Results with a series of analogues indicate that incorporation of the N in the new ring and the presence of an ether O at the 4-position are critical for enhanced activity.

  DOI：

  10.1021/jm00343a004

文献信息

• US4314054A
  申请人：——

  公开号：US4314054A

  公开（公告）日：1982-02-02
• [EN] COMPOSITIONS AND METHODS FOR TARGETED DELIVERY OF EFFECTOR MOLECULES<br/>[FR] COMPOSITIONS ET PROCEDES POUR LA LIBERATION CIBLEE DE MOLECULES EFFECTRICES
  申请人：——

  公开号：WO1996039183A1

  公开（公告）日：1996-12-12

  [EN] Targeting and effector molecules are conjugated by covalent attachment of the targeting molecule to the effector molecule by a combination of imine formation and thioalkylation. The conjugates are used in therapeutic or diagnostic applications to target the effector molecule to a desired cell or tissue. The immunoconjugates are particularly useful in the treatment of tumors, where, for example, antibody-doxorubicin conjugates are effective against doxorubicin resistant tumor cells.
  [FR] Des molécules de ciblage et effectrices sont conjuguées par fixation covalente de la molécule de ciblage à la molécule effectrice par une combinaison de formation d'imine et de thioalkylation. Les conjugués s'utilisent, dans des applications thérapeutiques ou diagnostiques, pour diriger la molécule effectrice vers une cellule ou un tissu désiré. Les immunoconjugués sont particulièrement utiles dans le traitement de tumeurs, là où, par exemple, les conjugués anticorps-doxorubicine sont efficaces contre les cellules tumorales résistant à la doxorubicine.
• Enhanced antitumor properties of 3'-(4-morpholinyl) and 3'-(4-methoxy-1-piperidinyl) derivatives of 3'-deaminodaunorubicin
  作者：Carol W. Mosher、Helen Y. Wu、Allan N. Fujiwara、Edward M. Acton

  DOI：10.1021/jm00343a004

  日期：1982.1

  Reductive N,N-dialkylation of daunorubicin with 2,2'-oxydiacetaldehyde and NaBH3CN occurred in two steps without interruption and with cyclization to form 3'-(4-morpholinyl)-3'-deaminodaunorubicin. This derivative retained the antitumor efficacy of doxorubicin against mouse leukemia P388 but at one-fortieth the dose; hence, it is the most potent anthracycline analogue synthesized so far. The 4-methoxy-1-piperidinyl derivative, similarly prepared with 3-methoxyglutaraldehyde, showed improved efficacy against P388, though at normal doses. Results with a series of analogues indicate that incorporation of the N in the new ring and the presence of an ether O at the 4-position are critical for enhanced activity.