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Increases in serum sulfate may explain some of the therapeutic effects of MSM, DMSO, and glucosamine sulfate. Organic sulfur, as SAAs, can be used to increase synthesis of S-adenosylmethionine (SAMe), glutathione (GSH), taurine, and N- acetylcysteine (NAC). MSM may be effective for the treatment of allergy, pain syndromes, athletic injuries, and bladder disorders. Other sulfur compounds such as SAMe, dimethylsulfoxide (DMSO), taurine, glucosamine or chondroitin sulfate, and reduced glutathione may also have clinical applications in the treatment of a number of conditions such as depression, fibromyalgia, arthritis, interstitial cystitis, athletic injuries, congestive heart failure, diabetes, cancer, and AIDS. Dosages, mechanisms of action, and rationales for use are discussed. The low toxicological profiles of these sulfur compounds, combined with promising therapeutic effects, warrant continued human clinical trails. Garlic has been used for centuries for disease prevention and treatment by several ethnic cultures. Epidemiologic investigations have found that risk of developing stomach, colon, and prostate cancers seems to be inversely related to garlic consumption. 4,5 Experimental animal and laboratory studies provide convincing evidence that garlic and some of its organosulfur components are effective inhibitors of a variety of cancers and cancer cells in culture, including those of breast, colon, skin, uterine, esophagus, and lung. 5,6 However, the specific component(s) of garlic that underlies the specific cellular and molecular events, which govern the anticancer properties, are not known with certainty. Depending on conditions of its cultivation, garlic can contain at least 33 different organosulfur compounds in addition to amino acids, vitamins, and micronutrients. The allyl sulfur compounds formed by enzymatic activity when garlic is minced or crushed, such as allicin, water-soluble S- allylmercaptocysteine (SAMC) and S-allylcysteine (SAC), and oil-soluble diallyl 10
disulfide (DADS) and diallyl sulfide (DAS), probably account for the majority of these 7, 8 anticancer effects. Summary A significant part of the present dissertation has been recently published. The work presented in this dissertation is concerned with the regioselective synthesis of functionalized 2-(arylthio)benzoates by cyclization of 3-arylthio-1-silyloxy-1,3- butadienes with 3-silyloxy-2-en-1-ones, 3-alkoxy-2-en-1-ones, 1,1- diacylcyclopropanes, and dimethyl acetylenedicarboxylate by formal [3+3] and [4+2] cyclization reactions mediated by TiCl4. 1. The first chapter includes the synthesis of functionalized 2-(phenylthio)benzoates, containing halogenated side chain, by domino ‘[3+3] cyclization / Homo-Michael′ reactions of 1-trimethylsilyloxy-3-arylthio-1,3-butadienes with 1,1- diacylcyclopropanes. In addition, 2-(phenylthio)benzoates are prepared by formal [3+3] cyclizations of1-trimethylsilyloxy-3-arylthio-1,3-butadienes with 3-silyloxy-2- en-1-ones. Some of the products were transformed into thioxanthones. 2. In the second chapter, a regioselective synthesis of 2-(arylthio)benzoates by the first [3+3] cyclizations of 3-arylthio-1-silyloxy-1,3-butadienes with 3-alkoxy-2-en-1- ones is reported. 3. In the third chapter, the synthesis of 5-arylthio-3-hydroxyphthalates by the first [4+2] cycloadditions of 3-arylthio-1-silyloxy-1,3-butadienes with dimethyl acetylenedicarboxylate is reported. 11
Page 1 and 2: Synthesis of functionalized 2-(aryl
Page 3 and 4: The ink of the scholar is more holy
Page 5 and 6: Affectionately Dedicated to “All
Page 7 and 8: Table of Contents 03 List of used a
Page 9 and 10: RCM Ring Closing Metathesis TBAI Te
Page 11 and 12: humans: 1) the thiomethyl of methio
Page 13: Chart 3. Structure of sumatriptan S
Page 17 and 18: 1. Synthesis of functionalized 2-(a
Page 19 and 20: 3-Arylthio-1-trimethylsilyloxy-1,3-
Page 21 and 22: under kinetic reaction control, by
Page 23 and 24: l a u 4-FC6H4 H Me H 40 m a v 4-FC6
Page 25 and 26: Table 2. Synthesis of thioxanthones
Page 27 and 28: 3a O OSiMe 3 O OMe + Me Me Cl 3TiO
Page 29 and 30: Table 3. Synthesis of 8a-x 3 7 8 Ar
Page 31 and 32: Cl + SPh OSiMe 3 3a 9 O OMe O O H i
Page 33 and 34: solution. The use of an excess (1.5
Page 35 and 36: Table 4. Synthesis of 12a-r 3 11 12
Page 37 and 38: 2.3 Conclusion In conclusion, I hav
Page 39 and 40: aromatization). An unseparable 1:2
Page 41 and 42: Table 5. Synthesis of arenes 14a-l
Page 43 and 44: 3.3 Conclusion In conclusion, I hav
Page 45 and 46: Mass Spectroscopy: AMD MS40, AMD 40
Page 47 and 48: 131.0 (ArCH), 132.7, 134.0, 135.9,
Page 49 and 50: (EI, 70 eV): m/z (%): 380 (100), 21
Page 51 and 52: (m), 1490 (m), 1434 (m), 1383 (w),
Page 53 and 54: 15.4, 16.9, 18.9 (CH3), 28.3 (CH2),
Page 55 and 56: (C). IR (neat): ν̃ = 2945 (w), 29
Page 57 and 58: 948 (w) 853 (m), 803 (m), 751 (m),
Page 59 and 60: 135.4, 139.2, 143.8, 146.5, 182.2 (
Page 61 and 62: Me S O Me Ph Br Methyl 4-methyl-5-(
Page 63 and 64: 35 Cl, 37 Cl, 61), 430 (M + , 35 Cl
Page 65 and 66:
ArH). 13 C NMR (62 MHz, CDCl3): δ
Page 67 and 68:
Me S O Me Me Methyl 4,6-dimethyl-5-
Page 69 and 70:
S Methyl 4-methyl-5-(2-bromoethyl)-
Page 71 and 72:
(CH2CH3), 33.3 (CH2), 40.1 (CH2), 5
Page 73 and 74:
Me 3,4-Dimethyl-2-phenylsulfanyl-be
Page 75 and 76:
Me 3,4-Dimethyl-2-(p-tolylsulfanyl)
Page 77 and 78:
OCH3), 7.08-7.17 (m, 7H, Ar); 13 C
Page 79 and 80:
(w), 750 (s), 732 (s), 688 (s), 650
Page 81 and 82:
35 Cl 35 Cl, 100), 359 (26), 357 (3
Page 83 and 84:
2924 (w), 2853 (w), 1728 (s), 1712
Page 85 and 86:
Me 3-Hydroxy-5-(4-methylphenylsulfa
Page 87 and 88:
Et 3-Hydroxy-5-(4-ethylphenylsulfan
Page 89 and 90:
(13), 264 (13), 262 (36) ,260 (12),
Page 91 and 92:
MS (EI, 70 eV): m/z (%) = 337 (16),
Page 93 and 94:
OH O 5'-Hydroxy-[1,1';3',1'']terphe
Page 95 and 96:
Refrences 1. Handbook of Chemistry
Page 97 and 98:
20. For a review of [3+3] cyclizati
Page 99 and 100:
Nationality Pakistan Place of Birth
Page 101 and 102:
Publications 1. Inam Iqbal, Muhamma
Page 103 and 104:
Tetrahedron 2007, 63, 12562-12575.
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List of used abbreviations - RosDok - Universität Rostock

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