2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide

• ChemBase编号: 6228
• 分子式: C12H15Cl2NO5S
• 平均质量: 356.2222
• 单一同位素质量: 355.00479895
• SMILES: C(Cl)(Cl)C(=O)N[C@H](CO)[C@H](O)c1ccc(cc1)S(=O)(=O)C
• Canonical SMILES: OC[C@H]([C@@H](c1ccc(cc1)S(=O)(=O)C)O)NC(=O)C(Cl)Cl
• InChI: InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1
• InChIKey: OTVAEFIXJLOWRX-NXEZZACHSA-N

名称和登记号

名称

• IUPAC标准名: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
• IUPAC传统名: thiamphenicol
• 别名: D-threo-2,2-Dichloro-N-(β-hydroxy-α-[hydroxymethyl]-4-[methylsulfonyl]phenethyl)acetamide; Thiamphenicol; THIAMPHENICOL; Thiophenicol; 2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide; D-d-threo-2-Dichloroacetamido-1-(4-methylsulfonylphenyl)-1,3-propanediol; Dextrosulphenidol; NSC 522822; Thiocymetin; Win 5063-2

登记号

• CAS号: 15318-45-3
• EC号: 239-355-3
• MDL号: MFCD00467983
• Beilstein号: 2819542
• PubChem SID: 24899874; 99445092; 160969653
• PubChem CID: 27200

理论计算性质

JChem

• Acid pKa: 7.6499147
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -0.22368595
• LogD (pH = 7.4): -0.38777936
• Log P: -0.22097217
• 摩尔折射率: 79.8796 cm^3
• 极化性: 31.870874 Å^3
• 极化表面积: 103.7 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.33
• LOG S: -2.2
• 溶解度: 2.27e+00 g/l

分子性质

理化性质

• 溶解度: DMSO; Ethanol; ethanol: soluble50 mg/mL, clear, colorless; Methanol
• 外观: White to Off-White Solid
• 熔点: 163-166 °C; 165-168°C

安全信息

• 保存条件: -20°C; -20°C Freezer, Under Inert Atmosphere
• RTECS编号: AB6680000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥99.0% (TLC)
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C12H15Cl2NO5S

详细说明

DrugBank - DB08621

Drug information: experimental

Selleck Chemicals - S2583

Research Area: Infection
Biological Activity:
Thiamphenicol (Thiophenicol) is an antimicrobial antibiotic and a methyl-sulfonyl analogue of chloramphenicol. Thiamphenicol (Thiophenicol) has a similar antibacterial spectrum to chloramphenicol. Thiamphenicol (Thiophenicol) inhibits protein synthesis in bacteria. Thiamphenicol (Thiophenicol) has a bacteriostatic action against a broad range of microorganisms, although it may be bactericidal for some species under some conditions, and in concentrations 3 to 5 times higher than the bacteriostatic concentrations. Thiamphenicol (Thiophenicol) is particularly used for the treatment of sexually transmitted infections and pelvic inflammatory disease. [1][2]References on Thiamphenicol (Thiophenicol)[1] Chemotherapy. , 1975, 21(2):73-81[2] http://en.wikipedia.org/wiki/Thiamphenicol, ,

Sigma Aldrich - T0261

Application
Thiamphenicol is an antibiotic that has been used to treat chancroid in men and uncomplicated gonorrhea1,2. It is used in studies of bacterial protein synthesis at the level of peptidyl transferase activity associated with the 23S rRNA of the 50S ribosomal subunit. It is used to study chloraniphenicol-thiamphenicol-resistance and the use of fluorinated analogs when resistance is encountered3.
Biochem/physiol Actions
Thiamphenicol inhibits mitochondrial protein synthesis of proteins such as cytochrome c oxidase.

Toronto Research Chemicals - T344160

Thiamphenicol is an antibiotic. Thiamphenicol is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Thiamphenicol is used particularly for the treatment of sexually transmitted infectio

参考文献

• Tikhonova, E., et al.: J. Biol. Chem., 279, 32116 (2004)
• Baucheron, S., et al.: J. Antimicrob. Chemother., 55, 707 (2004)
• Pages, J., et al.: Trends. Mol. Med., 11, 382 (2004)
• Lomovskaya, O., et al.: Biochem. Pharmacol., 71, 910 (2004)
• Samosorn, S.,