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Volumn 44, Issue 12, 2009, Pages 5006-5011

Known drug space as a metric in exploring the boundaries of drug-like chemical space

Author keywords

Aryl amines; Aryl nitro; Carcinogens; Drug like chemical space; Halogen atoms and drug development discovery; Known drug space; Marketed drug compounds; Nitrenium ions; Sulphur atoms

Indexed keywords

AROMATIC AMINE; HALOGEN; NITRO DERIVATIVE; SULFUR DERIVATIVE;

EID: 70449674250     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.08.014     Document Type: Article
Times cited : (32)

References (62)
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    • Ethanol has an Ionisation potential (IP) of 10.5 eV vs. 9.3 eV for ethanethiol and diethyl ether has an IP of 9.5 vs. 8.4 for diethylsulphide [32].
    • Ethanol has an Ionisation potential (IP) of 10.5 eV vs. 9.3 eV for ethanethiol and diethyl ether has an IP of 9.5 vs. 8.4 for diethylsulphide [32].
  • 33
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    • The measured Log P of benzene is 2.1 ± 0.1, fluorobenzene is 2.3 ± 0.2, chlorobenzene 2.8 ± 0.2, bromobenzene 3.0 ± 0.2, and finally iodobenzene 3.3 ± 0.2 [34]. Lipophilicity is clearly increased upon halogenation even though the dipole moment, which offsets this effect, is also increased by ∼1.7 Debye in all cases [35].
    • The measured Log P of benzene is 2.1 ± 0.1, fluorobenzene is 2.3 ± 0.2, chlorobenzene 2.8 ± 0.2, bromobenzene 3.0 ± 0.2, and finally iodobenzene 3.3 ± 0.2 [34]. Lipophilicity is clearly increased upon halogenation even though the dipole moment, which offsets this effect, is also increased by ∼1.7 Debye in all cases [35].
  • 37
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    • This has led to the introduction of the concept of lead-like chemical space where the molecular descriptors used generally have lower cut-off values than for drug-like chemical space [38,39
    • This has led to the introduction of the concept of lead-like chemical space where the molecular descriptors used generally have lower cut-off values than for drug-like chemical space [38,39].
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    • These include aliphatic thioesters, sulphonate esters, sulphur-sulphur single bonds, nitrogen-sulphur single bonds, thioureas, thiols, and thiazolidine-2,4-diones [11,12,41
    • These include aliphatic thioesters, sulphonate esters, sulphur-sulphur single bonds, nitrogen-sulphur single bonds, thioureas, thiols, and thiazolidine-2,4-diones [11,12,41].
  • 58
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    • The possibility of difficult synthetic routes and metabolic instability of compounds containing bromine and iodine can also play a role
    • The possibility of difficult synthetic routes and metabolic instability of compounds containing bromine and iodine can also play a role.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.