Organic Synthesis − Art or Science?

Rücker, Christoph; Rücker, Gerta; Bertz, Steven H.

doi:10.1021/ci030415e

Cited by 33 publications

(44 citation statements)

References 11 publications

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“…It meant ratio of multiple path count over path count and described the molecular shape. 12 The molecular shape had obvious effect on the diffusion of compound to the semi-permeable membrane. From the MLR model, the negative regression coefficient associated with this descriptor illustrated the lower value of PCR was beneficial for the compound diffusing across the membrane, leading to improvement of recovery.…”

Section: Discussionmentioning

confidence: 99%

Prediction of microdialysis relative recovery of flavone derivatives based on molecular descriptors

Zhan¹,

Huang²,

Shao³

et al. 2012

J. Braz. Chem. Soc.

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Recuperação relativa (R e ) é uma das principais preocupações de microdiálise, uma técnica de amostragem acessível que pode coletar continuamente drogas livres no sangue e na maioria dos tecidos. Para uma determinada sonda de microdiálise, a recuperação de cada composto desta sonda está relacionada às características estruturais e propriedades físico-químicas se as condições experimentais estão estabelecidas. Neste trabalho, modelos de relação quantitativa estrutura-propriedade (QSPR) utilizando os métodos de regressão linear múltipla (MLR) e máquina de vetores de suporte (SVM) foram ajustados com o intuito de destrinchar relações de R e de microdiálise de compostos e seus descritores moleculares que capturam as características estruturais moleculares para uma série de derivados da flavona. Como resultado, parâmetros estatísticos significativos (modelo MLR: R 2 = 0,9268 (coeficiente de correlação), Q 2 LOO = 0,8572 (variância explicada prevista) e Q 2 ext = 0,8639 (variância explicada externa), e modelo SVM: R 2 = 0,9383 e Q 2 ext = 0,8536) foram obtidos, indicando boa estabilidade e habilidade preditiva dos modelos. Assim, tornando viável prever as recuperações relativas na microdiálise de alguns compostos a partir de seus descritores moleculares. Este estudo foi uma tentativa inovadora e pode fornecer novos métodos para pesquisar a recuperação de microdiálise dos compostos.Relative recovery (R e ) is one of the major concerns of microdialysis, a valuable sampling technique which can continuously collect unbound drugs in blood and most tissues. For a given microdialysis probe, the recovery of every compound from the probe is related to its structural characteristics and physicochemical property if the experiment condition is fixed. In this work, quantitative structure-property relationship (QSPR) models using multiple linear regression (MLR) and support vector machine (SVM) methods were setup to excavate the relationships of microdialysis R e of compounds and their molecular descriptors which capture the structural characteristics of molecules for a series of flavone derivatives. As result, significant statistical parameters (MLR model: R 2 = 0.9268 (correlation coefficient), Q 2 LOO = 0.8572 (explained variance in prediction) and Q 2 ext = 0.8639 (external explained variance), and SVM model: R 2 = 0.9383 and Q 2 ext = 0.8536) were obtained, indicating good stability and predictive ability of the models. Therefore, it seems feasible to predict the microdialysis relative recovery of some compounds from their molecular descriptors. This investigation was an innovative trial and can provide new methods for researching the microdialysis recovery of the compounds.

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Section: Discussionmentioning

confidence: 99%

Prediction of microdialysis relative recovery of flavone derivatives based on molecular descriptors

Zhan¹,

Huang²,

Shao³

et al. 2012

J. Braz. Chem. Soc.

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“…For validity estimation, the bond priorities decided by between key-bonds and molecular complexity have been compared with eight compounds cited from an article (Fig. 4) [26], where the Rücker's molecular complexity index was used [19,27]. The index is called total walk count, abbreviated as twc.…”

Section: -2 Comparison Between Key-bonds and Molecular Complexitiesmentioning

confidence: 99%

Selective Search Focusing on Retro-Synthetically Important Bonds in A Synthesis Design System

Tanaka¹,

Kawai²,

Takabatake³

et al. 2009

J. Comput. Aided Chem.

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A new capability has been added to the synthesis design system SYNSUP [1]. The new module generates synthetic routes that focus on key-bonds. Key-bonds are selected according to their spatial relationships to chiral atoms and central atoms of functional groups. When the key-bonds cannot be formed by any reaction known to SYNSUP, then structure changes in the vicinity of the bonds are effected so that the key-bonds can be disconnected in a retro-synthetic pathway. We called the fashion "selective search". Such structure changes were studied, using 27 reported total synthesis of 25 naturally occurring compounds. This kind of selective search has been shown to be useful and practical for relatively complicated molecules.

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“…Starting from a chiral non-racemic , unsaturated aldehyde (31) and ethyl vinyl ether (32), Jacobsen and Chavez [58] showed that the chiral tridentate (Schiff base)Cr(III) (1S,2R)-(33) catalysed the hetero-Diels-Alder reaction to yield the cycloadduct (34) with excellent dr (>97:3) and ee (>99%) (Scheme 10). The use of the enantiomer (1R,2S)- (33) as catalyst resulted in a perceptible "mismatched" effect with the , -unsaturated aldehyde (31). This enantioselective reagent (1R,2S)-(33) still ensures the preferentially formation of a new diastereomer cycloadduct (35) with a useful level of diastereoselection dr (7:1).…”

Section: B -Diastereodivergencementioning

confidence: 99%

“…In this report, we would like to examine the complexity-and diversity-generating process in DOS from the angle of reaction-driven diversity (rather than complexity). Despite efforts to measure complexity [28][29][30][31], synthetic diversity has proved more amenable to quantification at the reaction level, in accordance with defined elements of diversity. In this review, three elements of diversity, i.e.…”

Section: Introductionmentioning

confidence: 99%