Germapharmaca: Some recent studies on biologically active organogermanium compounds

Recent research results on biologically active organogermanium compounds are described. Emphasis is placed on two categories based on (1) carbethoxyethylgermanium sesquioxide and (2) the ‘spirogermanium’ system. Other organogermanium derivatives covered include various mono-, di-, tri- and tetra-compounds. Mention is also made of organogermanium compounds as food additives and as the products of biological methylation.     

Comparative study of the biological activity of organosilicon and organogermanium compounds

The literature data and the results of our own investigations on the comparative study of the biological activity of isostructural organogermanium and organosilicon compounds have been summarized. It has been shown that the series of organogermanium and organosilicon compounds is more active than the carbon analogues, the majority of organogermanium compounds are less toxic than the sila analogues, the biological activity of the compounds under study appears to be similar but can dramatically differ in the degree of activity, and, moreover, in some particular cases sila and germa analogues exhibit the opposite biological effects.     

Synthesis,structures and in vitro anticancer activity of some germanium-substituted di-n-butyltin dipropionates

Organotin and organogermanium compounds are extensively studied for their wide range of biological activity. To link biological active properties of organotin and organogermanium, sixteen new germanium-substituted di-n-butyltin dipropionates with the form (R₃GeCHR¹CHR²COO)₂SnBu₂ⁿ·H₂O were synthesized.     

含α-氨基酸的新型有机锗化合物的合成与生物活性研究

设计合成了两个系列20个含α-氨基酸的新型有机锗化合物, 对化合物进行了波谱表征, 用X射线衍射测定了化合物Ph3GeCH(Ph)CH2CONHCH(CH2COOC2H5)COOC2H5的晶体结构. 抗肿瘤实验结果表明, 这两个系列的化合物有一定的抗KB, HCT-8和Bel-7402活性.     

Studies on the Interaction of Novel Organogermanium Sesquioxides with DNA

The affinity and mode of interaction of four novel organogermanium sesquioxides with calf thymus DNA(CT-DNA) and two synthetic oligonucleotides, d(AT)₂₂d(AT)₂₂ and d(GC)₂₂d(GC)₂₂, were investigated by a combination of absorption spectroscopy, DNA thermal denaturalization method, viscosity method, fluorometric technique, and competitive binding study with ethidium bromide(EB). The results show that the organogermanium compounds can interact with DNA by intercalation, the binding ability of the compounds to CT-DNA and the synthetic oligonucleotides was found to be modest(in comparison to the proven intercalators), with binding constants on the order of 10³―10⁵ L/mol, respectively. Generally, the binding of the organogermanium sesquioxides with naphthalene moiety to DNA is stronger than that of the compounds with anthraquinone moiety. And the compounds with anthraquinone moiety have preference for binding to AT-rich duplexes, whereas the compounds with naphthalene moiety have a little preference for binding to GC-rich duplexes. DNA may be the primary effect target.     

Isolation,Separation, and Preconcentration of Biologically Active Compounds from Plant Matrices by Extraction Techniques

Development of efficient methods for isolation and separation of biologically active compounds remains an important challenge for researchers. Designing systems such as organomineral composite materials that allow extraction of a wide range of biologically active compounds, acting as broad-utility solid-phase extraction agents, remains an important and necessary task. Selective sorbents can be easily used for highly selective and reliable extraction of specific components present in complex matrices. Herein, state-of-the-art approaches for selective isolation, preconcentration, and separation of biologically active compounds from a range of matrices are discussed. Primary focus is given to novel extraction methods for some biologically active compounds including cyclic polyols, flavonoids, and oligosaccharides from plants. In addition, application of silica-, carbon-, and polymer-based solid-phase extraction adsorbents and membrane extraction for selective separation of these compounds is discussed. Potential separation process interactions are recommended; their understanding is of utmost importance for the creation of optimal conditions to extract biologically active compounds including those with estrogenic properties.     

三烷氧基(β-酯基)乙基锗的合成及性质

生物及临床实验结果表明β-羧基乙基锗倍半氧化物[简式为(GeCH_2CH_2COOH)_2O_3]工具有抗癌等广泛的生物活性,且毒性极低。最近,我们又发现该化合物是一种具有双重性能的放射增敏剂,并合成了末见报道的类似物β-(N-芳基酰胺基)乙基锗倍半氧化物[简式(GeCH_2CH_2CONHAr)_2O_3],研究了其抗癌活性。本文所要报道的新有机锗化合物包括7个三烷氧基(β-酯基)乙基锗化合物[简式(R~2O)_3GeCH_2CHR~1COOR~2]和6个β-三氯锗基丙酸酯类化合物[简式Cl_3GeCH_2CHR~1COOR~2]。     

有机锗化合物的合成及其生物活性

讨论了有机锗化合物在国内外的进展。按制备方法分类,重点介绍了烃基锗化合物、螺锗及其衍生物、有机锗倍半氧化物、有机锗倍半硫化物、介吗川类有机锗化合笔挺人有生物活性的化合物。     

Investigation of innovative synthesis of biologically active compounds on the basis of newly developed reactions

Synthesis of biologically active compounds, including natural products and pharmaceutical agents, is an important and interesting research area since the large structural diversity and complexity of bioactive compounds make them an important source of leads and scaffolds in drug discovery and development. Many structurally and also biologically interesting compounds, including marine natural products, have been isolated from nature and have also been prepared on the basis of a computational design for the purpose of developing medicinal chemistry. In order to obtain a wide variety of derivatives of biologically active compounds from the viewpoint of medicinal chemistry, it is essential to establish efficient synthetic procedures for desired targets. Newly developed reactions should also be used for efficient synthesis of desired compounds. Thus, recent progress in the synthesis of biologically active compounds by focusing on the development of new reactions is summarized in this review article.     

Synthesis,Charcterization and Properties of Chlorodiphenylgermanium Dithiocarbamates

Organostannane and organosilane derivatives of dithiocarbamate are well-known. By contrast, analogous organogermanium compounds have not been studied.     

四配位有机锗化合物的红外光谱表征

对30多年所发表的四配位有机锗化合物的红外光谱进行了综合评论。即对饱和烃基锗、不饱和烃基锗、有机锗卤化合物、倍半氧锗化合物、其它这五类有机锗化合物的红外光谱作了系统的归纳，对光谱特征进行了总结。     

有机锗倍半氧化物及倍半硫化物的合成

有机锗化合物具有广谱药理活性,特别是抗肿瘤活性,其中有机锗倍半氧化物和倍半硫化物具有显著的抗癌活性。在我国这方面的研究却很少,为进一步研究有机锗的药理活性,我们合成了未见报道的一系列有机锗倍半氧化物和倍半硫化物,并分离了它们的中间体。     

四配位有机锗化合物的红外光谱表征

对 ３０ 多年所发表的四配位有机锗 化合物的红外光谱进行了综合 评论。即对饱和烃基 锗、不饱和 烃基锗、有机锗卤化 合物、倍半氧锗化合 物、其它这五类 有机锗化 合物的红 外光谱作 了系统的 归纳，对光谱特征进行了总结     

Synthesis and bioactivities of novel organogermanium sesquioxides containingα‐aminophosphonate groups

In order to search for novel antitumor drugs with high activity and low toxicity, a series of novel organogermanium sesquioxides containing α‐aminophosphonate groups were synthesized by the hydrolysis of O,O‐diphenyl N‐trichlorogermylpropiono‐α‐aminophosphonates. Their structures were confirmed by ¹H NMR, ³¹P NMR, and IR spectroscopy and by elemental analysis. Data of ¹H NMR and IR spectroscopy indicated that the title compounds are polymeric organogermanium sesquioxides. The results of bioassay showed that the products possess potential anticancer activities. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 209–212, 1999     

Reaction of the Dioxane Complex of Dichlorogermylene with Siloxanes

The major organogermanium compounds formed by reactions of the dioxane complex of dichlorogermylene with hexamethyldisiloxane, octamethyltrisiloxane, and hexamethyltricyclotrisiloxane are bis(trimethylsiloxy)dichlorogermane, 3,3-dichloro-1,1,1,5,5,7,7,7-octamethyl-3-germa-2,4,6-trioxa-1,5,7-trisilaheptane, and a cyclic germatetrasiloxane.     

Neurotropic activity of organogermanium compounds

Neurotropic activity of several classes of organogermanium compounds (namely germatranes, germanols, germsesquioxanes, germyladamantanes, germylamides, germylimides and germylsubstituted amines, imines and hydroxamic acids) and their synthesis are reviewed.     

Study of the composition of biologically active compounds in chaga meal. Perspectives of application of chaga meal in pharmaceutical industry

Methods of utilization of chaga meal are reviewed. Extraction of chaga meal with ethanol, chloroform, and tert-butyl methyl ether gives compounds possessing a high antioxidant activity. A wide spectrum of other biologically active compounds was found in these extracts. These compounds can be used for production of drugs and biologically active additives.     

IMINOSULFURANES FROM BIOLOGICALLY ACTIVE SULFONAMIDES AND RELATED COMPOUNDS

Abstract

Iminosulfuranes and iminosulfonium salts have been prepared from biologically active sulfonamides and other biologically active and related amino compounds. The new compounds have been characterized by nmr, uv, ir, mass spectra and elemental analysis. Deuterated analogs have also been prepared in selected cases for mass spectral comparison with their nondeuterated counterparts.     

合成有机锗倍半硫化物的新方法

有机锗倍半硫化物的合成是有机锗抗癌药物研究中的热点之一。在路易斯碱(如吡啶或三乙胺)存在下,经有机锗三氯化物溶液中通干燥的硫化氢气体制得有机锗倍半硫化物的方法有许多缺点,如无法计算吸收的硫化氢的量、设备复杂、操作困难并产生硫化氢臭味和毒性。我们用无水硫化钠直接与有机锗三氯化物作用即可得到有机锗倍半硫化物。利用此法合成了8种有机锗倍半硫化物:     

新型有机锗倍半氧化物及硫化物的合成

已先后合成的倍半氧化物类及倍半硫化物类化合物的前体,即有机锗三氯化物中只含1个锗原子。为了考查从含2个锗原子的前体合成的有机锗倍半氧化物及硫化物的药物活性,我们合成了1类化合物及相应的倍半氧化物(2类)及倍半硫化物(3类),并合成了酰基苯胺化合物1_e、2_e及3_e。结果见表1。