1,8-dihydroxybicyclo<7.3.1>trideca-4,9-diene-2,6-diyne-11,13-dione | 121444-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,8-dihydroxybicyclo<7.3.1>trideca-4,9-diene-2,6-diyne-11,13-dione
• 英文别名: (2S,5Z,9R)-2,9-dihydroxybicyclo[7.3.1]trideca-1(12),5-dien-3,7-diyne-11,13-dione
• CAS: 121444-01-7；134527-52-9
• 化学式: C₁₃H₈O₄
• 分子量: 228.204
• InChiKey: ARKCEWZPKPGESW-ASPPQYHASA-N

物化性质

• 沸点：
  520.2±50.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,8-dihydroxybicyclo<7.3.1>trideca-4,9-diene-2,6-diyne-11,13-dione 以82%的产率得到
  参考文献：
  名称：

  MANTLO, NATHAN B.;DANISHEFSKY, SAMUEL J., J. ORG. CHEM., 54,(1989) N2, C. 2781-2783

  摘要：

  DOI：
• 作为产物：
  描述：

  1,8-dihydroxyspirotrideca-4,9-diene-2,6-diyne-11,2'-<1,3>dioxolan>-13-one 生成 1,8-dihydroxybicyclo<7.3.1>trideca-4,9-diene-2,6-diyne-11,13-dione
  参考文献：
  名称：

  Observations in the Chemistry and Biology of Cyclic Enediyne Antibiotics:  Total Syntheses of Calicheamicin γ₁^I and Dynemicin A

  摘要：

  DOI：

  10.1021/jo951560x

文献信息

• Haseltine, John N.; Cabal, Maria Paz; Mantlo, Nathan B., Journal of the American Chemical Society, 1991, vol. 113, # 10, p. 3850 - 3866
  作者：Haseltine, John N.、Cabal, Maria Paz、Mantlo, Nathan B.、Iwasawa, Nobuharu、Yamashita, Dennis S.、Coleman, Robert S.、Danishefsky, Samuel J.、Schulte, Gayle K.

  DOI：——

  日期：——
• MANTLO, NATHAN B.;DANISHEFSKY, SAMUEL J., J. ORG. CHEM., 54,(1989) N2, C. 2781-2783
  作者：MANTLO, NATHAN B.、DANISHEFSKY, SAMUEL J.

  DOI：——

  日期：——
• A core system that simulates the cycloaromatization and DNA cleavage properties of calicheamicin-esperamicin: a correlation experiment
  作者：Nathan B. Mantlo、Samuel J. Danishefsky

  DOI：10.1021/jo00273a002

  日期：1989.6
• Methods
  申请人：Sattentau James Quentin

  公开号：US20070110759A1

  公开（公告）日：2007-05-17

  The presence of aldehydic groups on proteins and lipoproteins is associated with various pathological conditions such as atherosclerosis, diabetes and alcoholic liver disease. Respiratory syncytial virus (RSV) is a major cause of severe respiratory disease in infants and the elderly. RSV vaccine research has been impeded because a formalin-inactivated vaccine used in the 1960s predisposed infants to enhanced disease following subsequent natural infection. The molecular basis for the vaccine-induced hypersensitivity has not, however, been elucidated. We show here that addition of reactive carbonyl groups to ovalbumin (OVA) by treatment with glycolaldehyde or formaldehyde increases the protein's immunogenicity in mice, and biases the immune response towards a Th2-type response. The increased immunogenicity and the Th2-type response can both be abrogated by reductive elimination of the reactive carbonyl groups. We demonstrate that RSV inactivated by formaldehyde (FI-RSV), following a protocol used previously to prepare the vaccine, contains reactive carbonyl groups. Using a well-established model of FI-RSV vaccine-induced pathology, immunisation of mice with FI-RSV and subsequent challenge of the mice with live RSV induced Th2-type responses, lung eosinophilia and weight loss that were abrogated by reductive elimination of the reactive carbonyl groups. We thus propose that the addition of reactive carbonyl groups to RSV during inactivation is the major mechanism that drives the Th2-immune response and associated pathology. Moreover, we suggest that the addition of reactive carbonyl groups to other antigens, including vaccines, may be responsible for other hypersensitive and allergic reactions described in the literature.
• Observations in the Chemistry and Biology of Cyclic Enediyne Antibiotics:  Total Syntheses of Calicheamicin γ₁^I and Dynemicin A
  作者：Samuel J. Danishefsky、Matthew D. Shair

  DOI：10.1021/jo951560x

  日期：1996.1.1