QSAR of Steroids

Zeelen, F. J.

doi:10.1002/qsar.19860050402

Cited by 8 publications

(1 citation statement)

References 76 publications

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“…14 All these phenomena define the active conformation of the steroids, as Zeelen concluded more than two decades ago. 18 Molecular graphics observations on studied compounds 13 suggested that most of these structural changes can be better viewed along certain directions. The following composite molecular graphics descriptors were calculated:…”

Section: Molecular Graphics Descriptorsmentioning

confidence: 99%

Molecular graphics-structural and molecular graphics descriptors in a QSAR study of 17-alpha-acetoxyprogesterones

Kiralj¹,

Ferreira²

2003

J. Braz. Chem. Soc.

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Neste trabalho, foi feito um estudo de relações quantitativas entre a estrutura e a atividade biológica de 21 derivados de progesteronas ministrados via oral, dentre os quais 19 são 17-αacetoxiprogesteronas. O método de quadrados mínimos parciais foi usado para construir modelos de regressão de boa qualidade, com Q 2 = 0,707 e R 2 = 0,811 utilizando duas componentes principais e quatro descritores. A maioria dos descritores moleculares foi obtida a partir de gráficos moleculares das geometrias otimizadas por meio de cálculos ab initio com um conjunto de base DFT 6-31G** (descritores moleculares gráficos). Os outros descritores foram obtidos pela combinação dos descritores anteriores com parâmetros estruturais experimentais extraídos do complexo progesteronareceptor da progesterona (descritores gráfico-estruturais ou descritores gráficos e de modelagem). Os modelos de regressão empregando somente cinco descritores gráficos e três componentes principais foram satisfatórios, Q 2 =0,556, R 2 =0,718, demonstrando a utilidade dos mesmos em estudos QSAR. Neste trabalho, onde foram estudados derivados de progesterona, ficou evidente que os descritores moleculares gráficos descreveram com sucesso os efeitos conformacionais, estéreos e eletrônicos dos diferentes substituintes.Quantitative Structure-Activity Relationship study on 21 oral progestogens, 19 of which are 17α-acetoxyprogesterones, was performed by using Partial Least Squares. Fairly good regression models were achieved, the best being Q 2 =0.707, R 2 =0.811 with two Principal Components and four descriptors. Most of the molecular descriptors were generated from molecular graphics of DFT 6-31G** optimized geometries (molecular graphics descriptors) or were additionally combined with experimental structural parameters of progesterone receptor -progesterone complex (molecular graphics-structural, or molecular graphics and modeling descriptors). Regression models employing only these molecular graphics-based descriptors reached Q 2 =0.556, R 2 =0.718 with three Principal Components and five descriptors, demonstrating their usefulness in QSAR studies. In the case of progesterone derivatives, molecular graphics descriptors successfully included various conformational, steric and electronic substituent effects.

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Section: Molecular Graphics Descriptorsmentioning

confidence: 99%

Molecular graphics-structural and molecular graphics descriptors in a QSAR study of 17-alpha-acetoxyprogesterones

Kiralj¹,

Ferreira²

2003

J. Braz. Chem. Soc.

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Hormones, Sex Hormones

Gunnet

Dixon

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Progestins are a class of steroids named for their role in maintaining pregnancy. Naturally occurring progestins, such as progesterone, are 21‐carbon steroids having the basic pregnane structure. Synthetic progestins are derived from four structural groups; ie, 5α‐prenanes, 5α‐androstanes, estranes, and gonanes. They are produced by chemical and microbial degradation of naturally occurring steroids and by total synthesis. Structure–activity relationships of progestins have been explored using computer‐aided techniques. The principal use of progestins is in contraception, prescribed alone or in combination with estrogens, where they act primarily to prevent uncontrolled estrogen stimulation of the uterine endometrium. Progestins have other uses based on their antiestrogenic effects. They are known to cause a conformational change in receptors. When bound to an agonist, progestin receptors act as transcription factors, altering the rate of expression of various genes. New antiprogestins with improved receptor specificity are becoming available and may eventually be used in some of the same therapeutic areas as progestin agonists.

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References

1993

QSAR: Hansch Analysis and Related Approaches

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QSAR of Steroids

Cited by 8 publications

References 76 publications

Molecular graphics-structural and molecular graphics descriptors in a QSAR study of 17-alpha-acetoxyprogesterones

Molecular graphics-structural and molecular graphics descriptors in a QSAR study of 17-alpha-acetoxyprogesterones

Hormones, Sex Hormones

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