tert-butyl 4-(2-hydroxyethyl)imidazole-1-carboxylate | 211503-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 4-(2-hydroxyethyl)imidazole-1-carboxylate
• 英文别名: 1-N-Boc-4-(2-hydroxyethyl)imidazole
• CAS: 211503-47-8
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: JTNVPGGVUZJYSO-UHFFFAOYSA-N

物化性质

• 沸点：
  344.0±34.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(2-hydroxyethyl)imidazole-1-carboxylate 、 甲基磺酰氯 在 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-(2-methanesulfonyloxy-ethyl)-imidazole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  SYNTHESIS AND BIOLOGICAL ACTIVITY OF 2-FLUORO ADENINE AND 6-METHYL PURINE NUCLEOSIDE ANALOGS AS PRODRUGS FOR SUICIDE GENE THERAPY OF CANCER

  摘要：

  A novel series of 6-methylpurine nucleoside derivatives with substitutions at 5'-position have been synthesised. These compounds bear a 5'-heterocycle such as triazole or a imidazole with a two carbon chain, and an ether, thio ether or amine. To extend the SAR study of 2-fluoroadenine and 6-methyl purine nucleosides, their corresponding alpha-linker nucleosides with L-xylose and L-lyxose were also synthesized. All of these compounds have been evaluated for their substrate activity with E. coli PNP.

  DOI：

  10.1081/ncn-200059237
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 4-羟乙基咪唑 在 TEA 作用下， 以 甲醇 为溶剂， 生成 tert-butyl 4-(2-hydroxyethyl)imidazole-1-carboxylate
  参考文献：
  名称：

  SYNTHESIS AND BIOLOGICAL ACTIVITY OF 2-FLUORO ADENINE AND 6-METHYL PURINE NUCLEOSIDE ANALOGS AS PRODRUGS FOR SUICIDE GENE THERAPY OF CANCER

  摘要：

  A novel series of 6-methylpurine nucleoside derivatives with substitutions at 5'-position have been synthesised. These compounds bear a 5'-heterocycle such as triazole or a imidazole with a two carbon chain, and an ether, thio ether or amine. To extend the SAR study of 2-fluoroadenine and 6-methyl purine nucleosides, their corresponding alpha-linker nucleosides with L-xylose and L-lyxose were also synthesized. All of these compounds have been evaluated for their substrate activity with E. coli PNP.

  DOI：

  10.1081/ncn-200059237

文献信息

• [EN] PIPERIDINE, PYRROLIDINE AND 2-OXO-1,3-OXAZINANE DERIVATIVES AS INHIBITORS OF BACTERIAL EFFLUX-PUMPS FOR THE TREATMENT OF MICROBIAL INFECTIONS<br/>[FR] DÉRIVÉS DE PIPÉRIDINE, DE PYRROLIDINE ET DE 2-OXO-1,3-OXAZINANE EN TANT QU'INHIBITEURS DE POMPES À EFFLUX BACTÉRIENNES POUR LE TRAITEMENT D'INFECTIONS MICROBIENNES
  申请人：BASILEA PHARMACEUTICA AG

  公开号：WO2017093157A1

  公开（公告）日：2017-06-08

  The present invention relates to compounds of formula I or pharmaceutically acceptable salt, solvate or hydrate thereof wherein ASC is Ring A represents a 4- to 6-membered saturated ring containing carbon atoms as ring members in addition to the nitrogen atom, wherein a -CH 2 -CH 2 - moiety adjacent to the nitrogen atom is optionally replaced by a -C(=O)-O- moiety to form a carbamate; X represents a bond or -CH 2 -; AR1 and AR2 represent phenyl; R1, R2 and R3 represent independently hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; R4 represents hydrogen, halogen, C 1 -C 6 alkyl optionally substituted by 1 to 5 R10a, C 2 -C 6 alkenyl optionally substituted by 1 to 5 R10a, C 1 -C 6 alkylene-R10b, C 2 -C 6 alkenylene-R10b, C(O)OR11a, CHO, C(O)N(R12)R13 or O-R14; R5, R6 and R7 represent independently hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; R8 represents methyl or is absent, and when R8 is present the respective nitrogen atom carries a positive charge; R9a and R9b represent independently hydrogen or methyl; R10a represents independently at each occurrence halogen, hydroxyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; R10b represents C 3 -C 8 cycloalkyl, C(O)OR11a, CHO, C(O)N(R12)R13, N(R12)R13, Cycle-P or Cycle-Q; R11a and R11b represent independently at each occurrence hydrogen or C 1 -C 6 alkyl; R12 and R13 represent independently at each occurrence hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy-C 1 -C 4 alkyl; R14 represents C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkylene-Cycle-P, C 1 -C 6 alkylene-Cycle-Q; Cycle-P represents independently at each occurrence a saturated or partially unsaturated C 5 -C 6 carbocyclic ring optionally substituted by 1 to 3 R15 or a saturated or partially unsaturated 5- or 6-membered heterocyclic ring optionally substituted by 1 to 3 R15 containing carbon atoms as ring members and one or two ring members independently selected from N(R11b) and O; Cycle-Q represents independently at each occurrence phenyl optionally substituted by 1 to 3 R16 or a 5- to 6-membered heteroaryl ring containing one to four heteroatoms independently selected from O, S and N, optionally substituted by 1 to 3 R16; R15 and R16 represent independently at each occurrence halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; L1 represents -CH=CH-, -CH 2 -O-, -(CH 2 ) 2 -O-, -0-CH 2 -, -CH 2 -S-, -(CH 2 ) 2 -S-, -S-CH 2 -, -C(CH 3 ) 2 -, -(CH 2 ) 2 -or -CH=CH-CH 2 -; L2 represents C 1 -C 7 alkylene, wherein one or more -CH 2 - moieties in the alkylene moiety are optionally replaced independently by -C(=O)-, wherein within L2 there are no adjacent -C(=O)- moieties and wherein the terminal moiety of L2 is not -C(=O)-; and discloses their use in methods of treating a subject with a microbial infection or susceptible to a microbial infection in combination with an antimicrobial agent.

  本发明涉及具有式I的化合物或其药学上可接受的盐、溶剂或水合物，其中ASC是环A代表一个含有碳原子的4-至6-成员饱和环，除氮原子外，其中紧邻氮原子的-CH2-CH2-基团可以选择地被-C(=O)-O-基团取代以形成一个碳酸酯；X代表键或-CH2-；AR1和AR2代表苯基；R1、R2和R3分别代表氢、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基；R4代表氢、卤素、C1-C6烷基，可选地被1至5个R10a取代，C2-C6烯基，可选地被1至5个R10a取代，C1-C6烷基-R10b，C2-C6烯基-R10b，C(O)OR11a，CHO，C(O)N(R12)R13或O-R14；R5、R6和R7分别代表氢、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基；R8代表甲基或不存在，当R8存在时，相应的氮原子带有正电荷；R9a和R9b分别代表独立的氢或甲基；R10a在每次出现时独立地代表卤素、羟基、C1-C6烷氧基或C1-C6卤代烷氧基；R10b代表C3-C8环烷基，C(O)OR11a，CHO，C(O)N(R12)R13，N(R12)R13，Cycle-P或Cycle-Q；R11a和R11b在每次出现时独立地代表氢或C1-C6烷基；R12和R13在每次出现时独立地代表氢、C1-C4烷基、C1-C4卤代烷基或C1-C4烷氧基-C1-C4烷基；R14代表C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6卤代烯基、C1-C6烷基-Cycle-P、C1-C6烷基-Cycle-Q；Cycle-P在每次出现时独立地代表饱和或部分不饱和的C5-C6碳环环，可选择地被1至3个R15取代，或者由含有碳原子和一个或两个独立选择的N(R11b)和O的环成员的饱和或部分不饱和的5-或6-成员杂环环，可选择地被1至3个R15取代；Cycle-Q在每次出现时独立地代表苯环，可选择地被1至3个R16取代，或者由含有O、S和N的一个到四个杂原子的5-至6-成员杂环环，可选择地被1至3个R16取代；R15和R16在每次出现时独立地代表卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基；L1代表-CH=CH-、-CH2-O-、-(CH2)2-O-、-O-CH2-、-CH2-S-、-(CH2)2-S-、-S-CH2-、-C(CH3)2-、-(CH2)2-或-CH=CH-CH2-；L2代表C1-C7烷基，其中烷基基团中的一个或多个-CH2-基团可以独立地被-C(=O)-取代，在L2中没有相邻的-C(=O)-基团，并且L2的末端基团不是-C(=O)-；并且揭示了它们在联合抗菌剂治疗具有微生物感染或易感染微生物感染的受试者的方法中的用途。
• Bicyclic inhibitors of protein farnesyl transferase
  申请人：Warner-Lambert Company

  公开号：US06133303A1

  公开（公告）日：2000-10-17

  The present invention provides compounds of Formula (I). The present invention also provides a method of treating cancer and treating or preventing restenosis or atherosclerosis. Also provided by the present invention is a pharmaceutically acceptable composition containing a compound of Formula (I). ##STR1##

  本发明提供了化合物的结构式(I)。本发明还提供了一种治疗癌症、治疗或预防再狭窄或动脉粥样硬化的方法。本发明还提供了含有结构式(I)化合物的药学上可接受的组合物。
• BICYCLIC INHIBITORS OF PROTEIN FARNESYL TRANSFERASE
  申请人：Warner-Lambert Company LLC

  公开号：EP0966446B1

  公开（公告）日：2005-10-19
• US6133303A
  申请人：——

  公开号：US6133303A

  公开（公告）日：2000-10-17
• US6265422B1
  申请人：——

  公开号：US6265422B1

  公开（公告）日：2001-07-24