Isostere

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Classical Isosteres are molecules or ions with similar shape and often electronic properties. Many definitions are available. [1] but the term is usually employed in the context of bioactivity and drug development. Such biologically-active compounds containing an isostere is called a bioisostere. This is frequently used in drug design: [2] the bioisostere will still be recognized and accepted by the body, but its functions there will be altered as compared to the parent molecule.

History and additional definitions

Non-classical isosteres do not obey the above classifications, but they still produce similar biological effects in vivo. Non-classical isosteres may be made up of similar atoms, but their structures do not follow an easily definable set of rules.

The isostere concept was formulated by Irving Langmuir in 1919, [3] and later modified by Grimm. Hans Erlenmeyer extended the concept to biological systems in 1932. [4] [5] [6] Classical isosteres are defined as being atoms, ions and molecules that had identical outer shells of electrons, This definition has now been broadened to include groups that produce compounds that can sometimes have similar biological activities. Some evidence for the validity of this notion was the observation that some pairs, such as benzene, thiophene, furan, and even pyridine, exhibited similarities in many physical and chemical propertiesiea

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<span class="mw-page-title-main">Lanostane</span> Chemical compound

Lanostane or 4,4,14α-trimethylcholestane is a tetracyclic chemical compound with formula C
30
H
54
. It is a polycyclic hydrocarbon, specifically a triterpene. It is an isomer of cucurbitane.

<span class="mw-page-title-main">1,2,3,4,5-Cyclopentanepentol</span> Chemical compound

1,2,3,4,5-Cyclopentanepentol, also named cyclopentane-1,2,3,4,5-pentol or 1,2,3,4,5-pentahydroxycyclopentane is a chemical compound with formula C
5
H
10
O
5
or (–CHOH–)
5
, whose molecule consists of a ring of five carbon atoms, each connected to one hydrogen and one hydroxyl group. The unqualified term "cyclopentanepentol" usually refers to this compound. There are four distinct stereoisomers with this same structure.

<span class="mw-page-title-main">1,2,3,4-Cyclohexanetetrol</span> Chemical compound

1,2,3,4-Cyclohexanetetrol (also named cyclohexane-1,2,3,4-tetrol, 1,2,3,4-tetrahydroxycyclohexane, or ortho-cyclohexanetetrol) is an organic compound whose molecule can be described as a cyclohexane with four hydroxyl (OH) groups substituted for hydrogen atoms on four consecutive carbon atoms. Its formula can be written C
6
H
12
O
4
, C
6
H
8
(OH)
4
, or (–CH(OH)–)4(–CH
2
–)2.

<span class="mw-page-title-main">1,2,4,5-Cyclohexanetetrol</span> Chemical compound

1,2,4,5-Cyclohexanetetrol (also named cyclohexane-1,2,4,5-tetrol, 1,2,4,5-tetrahydroxycyclohexane, or para-cyclohexanetetrol) is an organic compound whose molecule can be described as a cyclohexane with four hydroxyl (OH) groups substituted for hydrogen atoms on two non-adjacent pairs of adjacent carbon atoms. Its formula can be written C
6
H
12
O
4
, C
6
H
8
(OH)
4
, or [–(CH(OH)–)2CH
2
–]2.

<span class="mw-page-title-main">2-(Ethylamino)-1,2-diphenylethanone</span> Chemical compound

2-(Ethylamino)-1,2-diphenylethanone is a chemical compound which was first invented in 1955, researched by ICI in 1969 as an antidepressant, and subsequently claimed by AstraZeneca as an inhibitor of the enzyme 11β-Hydroxysteroid dehydrogenase type 1. No other pharmacological data has been disclosed, though its chemical structure closely resembles that of certain designer drug compounds such as ephenidine and N-ethylhexedrone.

References

  1. Richard Silverman, The Organic Chemistry of Drug Design and Drug Action, Second Edition, 2004
  2. Nathan Brown. Bioisosteres in Medicinal Chemistry. Wiley-VCH, 2012, p. 237. ISBN   978-3-527-33015-7
  3. Irving Langmuir. Isomorphism, isosterism and covalence. J. Am. Chem. Soc.1919, 41, 1543-1559. doi : 10.1021/ja02231a009
  4. Mukesh Doble, Anil Kumar Kruthiventi, Vilas Gajanan. Biotransformations and Bioprocesses. CRC Press, 2004, p. 60. ISBN   0-8247-4775-5
  5. H. Erlenmeyer, Ernst Willi: Zusammenhänge zwischen Konstitution und Wirkung bei Pyrazolonderivaten. In: Helvetica Chimica Acta. 18, 1935, S. 740, doi : 10.1002/hlca.193501801101.
  6. Hans Erlenmeyer, Martin Leo: Über Pseudoatome. In: Helvetica Chimica Acta. 15, 1932, S. 1171, doi : 10.1002/hlca.193201501132.