β-hematin | 885624-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: β-hematin
• CAS: 885624-25-9
• 化学式: C₆₈H₆₂Fe₂N₈O₈
• 分子量: 1230.98
• InChiKey: HXEIDFYYVJVSGW-AWOXZACZSA-H

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  hemin 在 2,6-二甲基吡啶 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 504.0h， 生成 β-hematin
  参考文献：
  名称：

  消除疟疾颜料中的双丙酸酯缺口：铁（III）（氘卟啉）二聚体中的新结构基序

  摘要：

  用DMSO /甲醇中的非配位碱处理氘铁血红素，氯（氘代铁卟啉）铁（III）可以分离[（氘代铁卟啉）铁（III）] 2，是一种氘代血红素酐（DHA），一种与疟疾色素类似的物质，它是疟疾引起的血红素解毒的天然产物。通过X射线粉末衍射分析已解决了从该溶剂系统获得的DHA的结构，并显示了与疟疾色素的许多相似之处，但仍存在重要的结构差异。最值得注意的是，溶剂化的水分子占据了由丙酸酯侧链产生的缺口，并稳定了与长的Fe-O键配位的显着弯曲的丙酸酯配体，并生成了与水分子相关的羧酸盐簇。这些特征加在一起，说明了其增加的溶解度和更开放的结构，并增加了卟啉-卟啉的分离。与该结构相关的红外光谱特征也说明了1587 cm -1处的强红外波段在许多合成疟疾色素的无定形制剂中可以看到这种现象，因此建议稳定这些结构可能是抗疟药的新目标。乙烯基取代基在该生物化学中的重要作用进一步通过单晶X射线衍射分析获得的氘铁血红素的结构得到了证明。

  DOI：

  10.1002/chem.201805116

文献信息

• The Role of the Four Stereoisomers of the Heme Fe–O Cyclic Dimer in the Crystalline Phase Behavior of Synthetic Hemozoin: Relevance to Native Hemozoin Crystallization
  作者：Tine Straasø、Sergey Kapishnikov、Kenichi Kato、Masaki Takata、Jens Als-Nielsen、Leslie Leiserowitz

  DOI：10.1021/cg200410b

  日期：2011.8.3

  Hemozoin is a crystalline byproduct formed upon host hemoglobin digestion in malaria-infected blood cells, crucial for parasitic survival. On the basis of published spectroscopic and X-ray powder diffraction (XRPD) data, hemozoin is believed to be very similar to the synthetic compound beta-hematin, which consists of cyclic centrosymmetric dimers of ferriprotoporphyrin IX [Fe(3+) PPIX] molecules coordinated via Fe-O bonds. The enantio-facial symmetry of Fe(3+) PPIX implies, however, that four different Fe-O cyclic stereoisomers, two centrosymmetric and two chiral, of opposite handedness, should be formed in the crystallizing solution of beta-hematin. A low-temperature XRPD study of beta-hematin, i.e. synthetic hemozoin, revealed the presence, not only of the published phase (Pagola, S.; Stephens, P. W.; Bohle, D. S.; Kosar, A. D.; Madsen, S. K. Nature 2000, 404, 307) but also of a minor phase. We propose, based on Rietveld refinement and DFT+vdW computations (companion manuscript, DOI: 10.1021/cg200409d), that the minor phase consists mainly of the second centrosymmetric isomeric type in a crystal structure similar to that of the major phase. The enantiomeric chiral isomers may, on symmetry grounds, be enantioselectively occluded into the growing crystals, introducing disorder. The chiral dimers, on being first adsorbed on the crystal faces, would act as tailor-made additives, retarding crystal growth, which also explains the crystalline micrometer size. The existence of two phases in beta-hematin may be crucial for a fuller understanding and more complete determination of the crystal structure of hemozoin, of which only one phase has crystallized according to published data.
• Synthesis, Characterization, and Pharmacological Evaluation of Silicon-Containing Aminoquinoline Organometallic Complexes As Antiplasmodial, Antitumor, and Antimycobacterial Agents
  作者：Yiqun Li、Carmen de Kock、Peter J. Smith、Hajira Guzgay、Denver T. Hendricks、Krupa Naran、Valerie Mizrahi、Digby F. Warner、Kelly Chibale、Gregory S. Smith

  DOI：10.1021/om300945c

  日期：2013.1.14

  Two silicon-containing analogues (1, 2) of chloroquine, modified in the lateral side chain with organosilicon moieties, were synthesized. Compounds 1 and 2 were further reacted with dinuclear half-sandwich transition metal precursors [Ru(Ar)(mu-Cl)Cl](2) (Ar = eta(6)-p-(PrC6H4Me)-Pr-i; eta(6)-C6H6; eta(6)-C6H5OCH2CH2OH), [Rh(COD)(mu-Cl)](2), and [RhCp*(mu-Cl)Cl](2), to yield a series of neutral mononuclear Ru(II), Rh(I), and Rh(III) silicon-aminoquinoline complexes (3-12). Compounds 1 and 2 act as monodentate donors that coordinate to the transition metals via the quinoline nitrogen of the aminoquinoline scaffold. All the compounds were characterized using various analytical and spectroscopic techniques, and the molecular structures of compounds 2 and 11 were elucidated by single-crystal X-ray diffraction analysis. Furthermore, the in vitro pharmacological activities of compounds 1-12 were established against chloroquine-sensitive (NF54) and chloroquine-resistant (Dd2) strains of the malarial parasite Plasmodium falciparum and against the pathogenic bacterium Mycobacterium tuberculosis H37Rv, as well as an esophageal (WHCO1) cancer cell line.