利用含硼酯異腈化合物合成ugi四組成反應衍生物(I):
在傳統的藥物開發中，含硼分子顯少被列入考慮，近幾年在藥物合成上，不再侷限於一般天然物中含有的元素。硼，亦被使用在藥物合成中，近來研究發現含硼藥物分子對其所作用之生化目標具有高度選擇性與高度活性等優點，使許多研究單位逐漸積極投入含硼藥物之開發。
本研究講述兩種合成含硼甲基醯胺化合物之合成方法( Scheme 1 )，並討論兩種方法之優缺比較，將上述的含硼甲基醯胺化合物成功合成出含硼酯異腈化合物 ( Scheme 2 )。並間接利用含硼異腈化合物進行Ugi-4CR反應( Scheme 3 )，嘗試成功合成出含單硼原子化合物。
合成含硼酯之甲基醯胺異腈衍生物(II):
本研究目的在於開發適用於硼中子捕獲治療的藥物，鑒於硼中子捕獲治療的重要性並結合Ugi reaction的廣泛應用性，且成功合成出含硼之化合物 ( Scheme 4 )，期望能對癌症治療有進一步的發展。而後將所得之化合物進行一系列的藥物化學結構，找出作為後續藥物開發的領導藥物。此外，甲基醯胺官能基亦能轉成異腈結構( Scheme 5 )，提高分子多樣性及生物多樣性。
合成含硼之甲基醯胺四氮唑衍生物 (III):
    雜環化合物是一類具有藥理活性的小分子化合物，例如四氮唑衍生物可做為抗腫瘤、抗過敏活性，亦可減緩肝臟代謝率，進而增加生物利用度，根據上述所合成出的含硼酯之甲基醯胺異腈，可藉由TMS-N3轉換成含硼之甲基醯胺四氮唑衍生物( Scheme 6 )，提供一個新的含硼分子合成路徑，並且增加了異腈化合物的廣用性。

The boron analogs are less considered as pharmaceutical agents. However, the approval of Bortezomib ( velcadeTM ) has encouraged medicinal chemists to put an effort on discovering boron-containing drugs. In the first part of this thesis, I will talk about the synthesis of boron-containing formamide via two different synthetic strategies ( Scheme 1 ). Their advantages and disadvantages will be included as well. After successfully obtained the desired boron-containing formamides, these analogs were transformed to the corresponding isocyanides through dehydration process ( Scheme 2 ). With these boron-containing isocyanides in hand, the microwave-assisted Ugi-4CR was employed to construct series of amidomethyl isocyano boronate esters ( Scheme 3 ). 
In the second part of my thesis, I successfully synthesized boron-containing formyl compounds via Ugi-
3CR ( Scheme 4 ), These compounds were then converted to the corresponding boron-containing amidomethyl isocyanides ( Scheme 5 ).Heterocycles are often appears in many biological active nature products, which possess interesting medicinal properties (i.e. such as spasmolytic, diuretic, anticoagulant, anticancer, and antianaphylactic activities.), hence, they are considered as an important class of functional group in medicinal chemistry. In the third part of my thesis, I will utilize the amidomethyl isocyano boronate ester analogs, which were synthesized from the previous chapter, to construct series of the corresponding tetrazoles.  ( Scheme 6 ). These compounds were currently under biological evaluations, and the results will be reported in the future.

主目錄 
Chapter 1利用含硼酯異腈化合物合成ugi四組成反應衍生物(I):1
1.1異腈化合物之介紹...........................................................1
1.2含硼化合物之介紹....................................................................7
1.2.1硼元素之化學特性 .........................................................7
1.2.2含硼化合物之合成應用...............................................10
1.3含硼異腈化合物之介紹..........................................................11
1.4含硼藥物在硼中子捕獲治療(Boron Neutron Capture Therapy,BNCT)上的應用...........................................................13
1.4.1 BNCT簡介...................................................................13
1.4.2 BNCT藥物介紹...........................................................14
1.5結果與討論..............................................................................16
1.5.1 含硼Ugi之合成..........................................................16
1.5.2含硼甲醯胺化合物之合成............................................17
1.5.3含硼異腈化合物之合成 ...............................................21
1.5.4結論...............................................................................23
Chapter 2合成含硼酯之甲基醯胺異腈衍生物(II):............................ 24 
2.1含硼藥物之介紹.............................................................24
2.1.1含硼化合物在藥物化學之應用............................26
2.2 Ugi多組成反應之介紹..................................................27
2.2.1 Ugi多組成反應之藥物應用.................................31
2.3異腈化合物之介紹.........................................................32
2.4 結果與討論.............................................................................36
2.4.1 含硼Ugi之合成 ..........................................................36
2.4.2 含硼酯之甲基醯胺異腈衍生物之合成.......................40
2.4.3討論...............................................................................44
Chapter 3合成含硼之甲基醯胺四氮唑衍生 ...................................... 45 
3.1四唑化合物之介紹..................................................................45
3.2四唑化合物之合成..................................................................48
3.2.1疊氮化物與腈類化合物環化........................................48
3.2.2疊氮化物與胺類化合物環化........................................49
3.2.3疊氮化物與酰胺類化合物環化....................................50
3.2.4 1-substituted tetrazole之合成.....................................50
3.2.5 2-substituted tetrazole之合成.....................................52
3.2.6 5-substituted tetrazole之合成.....................................53
3.3 結果與討論.............................................................................57
3.3.1含硼四唑化合物之合成...............................................57
3.4 總結........................................................................................60
Chapter 4實驗藥品與實驗儀器 .......................................................... 61 
4.1使用藥品.................................................................................61
4.2實驗儀器與測試方法..............................................................63
Chapter 5實驗步驟 ............................................................................. 64 
5.1含硼異腈化合物之合成..........................................................64
5.2含硼甲醯基化合物之合成......................................................68
5.3含硼Ugi化合物之合成..........................................................72
5.4含硼酯之甲基醯胺異腈衍生物之合成 ...................................79
5.5含硼之甲基醯胺四氮唑衍生物之合成...................................85
附錄一 附圖 ....................................................................................... 87 
附錄二 參考資料 .....................................................................112
附圖目錄
附圖 1 化合物 U01 之1H-NMR (600 MHz, CDCl3-d) .................... 89 
附圖 2 化合物 U01 之13C-NMR (150 MHz, CDCl3-d) ................... 89 
附圖 3 化合物 U01 之11B-NMR (192.5 MHz, CDCl3-d) ................ 90 
附圖 4 化合物 U02 之1H-NMR (600 MHz, CDCl3-d) .................... 90 
附圖 5 化合物 U02 之13C-NMR (150 MHz, CDCl3-d) ................... 91 
附圖 6 化合物 U02 之11B-NMR (192.5 MHz, CDCl3-d) ................ 91 
附圖 7 化合物 U02 之HRMS(ESI,positive ion)【M+H】^+ ........ 92 
附圖 8 化合物 U03 之1H-NMR (600 MHz, CDCl3-d) .................... 92 
附圖 9 化合物 U03 之13C-NMR (150 MHz, CDCl3-d) ................... 93 
附圖 10 化合物 U03 之1B-NMR (192.5 MHz, CDCl3-d) ................ 93 
附圖 11 化合物 U04 之1H-NMR (600 MHz, CDCl3-d) .................. 94 
附圖 12 化合物 U04 之1C-NMR (150 MHz, CDCl3-d) .................. 94 
附圖 13 化合物 U04 之1B-NMR (192.5 MHz, CDCl3-d) ................ 95 
附圖 14 化合物 U04 之HRMS(ESI,positive ion)【M+H】^+ ...... 95 
附圖 15 化合物 U05 之1H-NMR (600 MHz, CDCl3-d) .................. 96 
附圖 16 化合物 U05 之1C-NMR (150 MHz, CDCl3-d) .................. 96 
附圖 17 化合物 U05 之1B-NMR (192.5 MHz, CDCl3-d) ................ 97 
附圖 18 化合物 U06 之1H-NMR (600 MHz, CDCl3-d) .................. 97 
附圖 19 化合物 U06 之13C-NMR (150 MHz, CDCl3-d) ................. 98 
附圖 20 化合物 U06 之11B-NMR (192.5 MHz, CDCl3-d) .............. 98 
附圖 21 化合物 C01 之1H-NMR (600 MHz, CDCl3-d) .................. 99 
附圖 22 化合物 C01 之13C-NMR (150 MHz, CDCl3-d) ................. 99 
附圖 23 化合物 C01 之11B-NMR (192.5 MHz, CDCl3-d) ........... 100 
附圖 24 化合物 C01 之HRMS(ESI,positive ion)【M+H】^+ .... 100 
附圖 25 化合物 C02 之1H-NMR (600 MHz, CDCl3-d) ................ 101 
附圖 26 化合物 C02 之13C-NMR (150 MHz, CDCl3-d) ............... 101 
附圖 27 化合物 C02 之11B-NMR (192.5 MHz, CDCl3-d) ............ 102 
附圖 28 化合物 C02 之HRMS(ESI,positive ion)【M+H】^+ .... 102 
附圖 29 化合物 C03 之1H-NMR (600 MHz, CDCl3-d) ................ 103 
附圖 30 化合物 C03 之13C-NMR (150 MHz, CDCl3-d) ............... 103 
附圖 31 化合物 C03 之11B-NMR (192.5 MHz, CDCl3-d) ............ 104 
附圖 32 化合物 C03 之HRMS(ESI,positive ion)【M+H】^+ .... 104 
附圖 33 化合物 C04 之1H-NMR (600 MHz, CDCl3-d) ................ 105 
附圖 34 化合物 C04 之13C-NMR (150 MHz, CDCl3-d) ............... 105 
附圖 35 化合物 C04 之11B-NMR (192.5 MHz, CDCl3-d) ............ 106 
附圖 36 化合物 C05 之1H-NMR (600 MHz, CDCl3-d) ................ 106 
附圖 37 化合物 C05 之13C-NMR (150 MHz, CDCl3-d) ............... 107 
附圖 38 化合物 C05 之13C-NMR (150 MHz, CDCl3-d) ............... 107 
附圖 39 化合物 C05 之HRMS(ESI,positive ion)【M+H】^+ .... 108 
附圖 40 化合物 C06 之1H-NMR (600 MHz, CDCl3-d) ................ 108 
附圖 41 化合物 C06 之13C-NMR (150 MHz, CDCl3-d) ............... 109 
附圖 42 化合物 C06 之11B-NMR (192.5 MHz, CDCl3-d) ............ 109 
附圖 43 化合物 T01 之1H-NMR (600 MHz, CDCl3-d) ................ 110 
附圖 44 化合物 T01 之13C-NMR (150 MHz, CDCl3-d) ............... 110 
附圖 45 化合物 T01 之11B-NMR (192.5 MHz, CDCl3-d) ........... 111 

圖表目錄
Fig. 1.1 含異腈之天然化合物............................................................2
Fig. 1.2 含有拉電子基團之異腈........................................................4
Fig. 1.3 異腈聚合反應生成polyiminomethylenes...........................6
Fig. 1.4 常見硼酸型態：....................................................................8
Fig. 1.5 常見硼酯型態：....................................................................9
Fig. 1.6 常見硼酸鹽類型態：..........................................................10
Fig. 1.7 BNCT藥物(a) BPA  (b) BSH..........................................15
Table. 1.1 含硼甲醯胺類化合物之合成路徑A、路徑B產率 .......20
Table. 1.2 含硼異腈化合物 .............................................................22
Scheme 1.1 兩種不同構型的異腈.....................................................1
Scheme 1.2 Isocyanide之加成反應式...............................................3
Scheme 1.3 Carbene之加成反應式...................................................3
Scheme 1.4 Carbon monoxide之加成反應式...................................3
Scheme 1.5 抑制劑K252a之合成途徑.............................................4
Scheme 1.6 與路易氏鹼反應生成α-metalated isocyanides途徑....5
Scheme 1.7與路易氏鹼形成α-metalated isocyanides之應用.........5
Scheme 1.8 Schöllkopf與van Leusen在異原環上之合成...............6
Scheme 1.9 硼酸化合物在四面體轉換 ..............................................7
Scheme1.10 硼酸化合物於cross-coupling之反應........................10
Scheme 1.11 硼酸化合物於Petasis reaction之反應......................11
Scheme 1.12含硼之異腈化合物合成過程.......................................12
Scheme 1.13 穩定含硼之異腈化合物..............................................12
Secheme 1.14Ugi-4CR Analogs........................................................13
Secheme 1.15 Ugi-4CR reaction.......................................................16
Secheme 1.16 含硼化合物之合成步驟............................................17
Secheme 1.17 含硼一級醇化合物之簡化合成步驟........................18
Secheme 1.18 含硼甲醯胺化合物之合成路徑 ................................19
Scheme 1.19 脫水反應 .....................................................................21
Fig. 2.1 市售含硼藥物Bortezomib（Velcade）的化學結構………24
Fig. 2.2 含硼藥物結構(a) Vancomycin (b) Cyclosporin (c) Bleomycin.........................................................................................25
Fig. 2.3 含硼小藥物分子在治療疾病上的應用...............................27
Fig. 2.4 (a)Linear approach (b)Convergent Approach...................28
Fig. 2.5 理想的有機合成策略..........................................................29
Fig. 2.6 雙官能基之起始物在Ugi reaction之應用........................31 
Fig. 2.7 含Aminomethyl結構之藥物.............................................32
Fig. 2.8 合成含硼Ugi衍生物..........................................................39
Fig 2.9 含硼之甲基醯胺四氮唑衍生物之產物...............................43
Table. 2.1 其他重要的異腈合成反應…………………….………...35
Table. 2.2 合成含硼Ugi系列之測試表..........................................37
Table. 2.3 合成含硼之Ugi化合物之整理......................................38
Table 2.4 含硼Ugi-3CR之優化條件..............................................41
Table 2.5含硼之甲基醯胺四氮唑衍生之合成.................................42
Scheme 2.1 Ugi多組成反應…………….………. ….. ….. …… …. 30
Scheme 2.2 Ugi多組成反應之反應機構..........................................30
Scheme 2.3異腈合成以及水解過程................................................33
Scheme 2.4 Hofmann的異腈合成法...............................................33
Scheme 2.5 合成硼酯之Ugi化合物...............................................37
Scheme 2.6脫水反應 ........................................................................41
Fig. 3.1雜環藥物之結構………………………………………….. ..45
Fig 3.2 (a) Olmesartan Medoxomil, (b) Candesartan Cilexetil......46
Fig 3.3含四唑雜環藥物結構............................................................47
Fig 3.4具有抗發炎以及抗細菌之生物活性之含四唑雜環化合物.47

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