7-azidoheptanoyl chloride | 135920-29-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 7-azidoheptanoyl chloride
• CAS: 135920-29-5
• 化学式: C₇H₁₂ClN₃O
• 分子量: 189.645
• InChiKey: FYSWSHPUCLDSTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-azidoheptanoyl chloride 在 copper(II) sulfate 、 sodium ascorbate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 生成 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 6-(1-(6-(2-amino-1H-imidazol-4-yl)hexyl)-1H-1,2,3-triazol-4-yl)hexyl(2-(pyridin-2-yl)ethyl)carbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-aminoimidazole/carbamate hybrid anti-biofilm and anti-microbial agents

  摘要：

  The successful marriage of structural features from our 2-aminoimidazole and menthyl carbamate classes of anti-biofilm agents has resulted in the development of a novel hybrid scaffold of biofilm modulators. The compounds were evaluated against a panel of four bacterial strains for anti-biofilm and anti-microbial activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.057
• 作为产物：
  描述：

  7-叠氮庚酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 7-azidoheptanoyl chloride
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-aminoimidazole/carbamate hybrid anti-biofilm and anti-microbial agents

  摘要：

  The successful marriage of structural features from our 2-aminoimidazole and menthyl carbamate classes of anti-biofilm agents has resulted in the development of a novel hybrid scaffold of biofilm modulators. The compounds were evaluated against a panel of four bacterial strains for anti-biofilm and anti-microbial activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.057

文献信息

• 4-Substituted alkyl carbapenem antibiotics
  申请人：Bristol-Myers Squibb Company

  公开号：EP0433759A1

  公开（公告）日：1991-06-26

  Compounds of the formula wherein R1 is hydrogen, C1-2 alkyl, -CH20H, -CH2NH2, A is an unsubstituted or hydroxy-substituted straight or branched C, -, 10 alkylene group or a straight or branched C1-10 alkylene group having an intervening heteroatom selected from oxygen, sulfur and nitrogen; R2 is hydroxy, halogen, C1-4 alkoxy, nitrile, azido, a quaternary ammonio group, -NRSR6, azetidinyl, or a 5- or 6-membered heterocyclic group selected from heteroaromatic and heteroalicyclic joined through a carbon atom thereof; B is a straight or branched C, -6 alkylene group or a direct bond when R3 is joined to the sulfur atom through a carbon atom thereof; R3 is a residue of an organic group; R4 is hydrogen, a removable carboxy-protecting group or a physiologically hydrolyzable ester group; R5 and R6 each are independently hydrogen, C1-6 alkyl, C1-4 alkoxy, hydroxyethyl, azidoethyl, aminoethyl, and when R5 is hydrogen or C, -a alkyl, R6 is hydroxy, C1-4 alkoxy, amino, C1-4 alkylamino, di(Ci-4.)alkylamino, substituted C1-4 alkyl wherein said alkyl substituent is selected from hydroxy, azido, amino, guanidino, nitrile, carboxy, formimidoyl and phenyl, or an acyl residue of an amino acid or peptide; or R5 and R6, taken together with the nitrogen atom to which they are attached, is an unsubstituted or substituted heterocyclic ring having 1 to 2 ring members and having up to four heteroatoms in each ring independently selected from oxygen, nitrogen and sulfur, wherein said substituent is selected from the group consisting of C1-4 alkyl, C1-4 alkoxy, trifluoromethyl, hydroxy, halogen, amino, nitrile, carboxy, carbamido, carbamoyl, C, -4 alkylamino and amino (C1-4) alkyl; W is a direct bond, oxygen, sulfur or NR'°; Y is oxygen or NR10; Z is hydrogen, hydroxy, C1-4 alkyl, C1-4 alkoxy, -NR7R8, amino(C1-4)alkyl, azido(C1-4)alkyl or hydroxy (C1-4)alkyl; R7 and R8 each are independently hydrogen, C1-4 alkyl or alkanoyl; and R10 is hydrogen, C1-4 alkyl, C1-4 alkylamino or di(C1-4)alkylamino; or a non-toxic pharmaceutically acceptable salt thereof, are novel antimicrobial agents which are useful in the treatment of infectious disease in humans and other animals. Novel intermediates and processes for their preparation are also disclosed.

  式中的化合物 其中 R1 为氢、C1-2 烷基、-CH20H、-CH2NH2、 A 是未取代的或羟基取代的直链或支链 C,-,10-亚烷基，或具有选自氧、硫和氮的杂原子的直链或支链 C1-10 亚烷基； R2 是羟基、卤素、C1-4 烷氧基、腈、叠氮、季铵基、-NRSR6、 氮杂环丁基，或通过一个碳原子连接的 5 或 6 元杂环基团，这些杂环基团选自杂芳族和杂脂环； B 是直链或支链 C, -6 亚烷基，或当 R3 通过其碳原子与硫原子相连时的直接键； R3 是有机基团的残基； R4 是氢、可去除的羧基保护基团或生理上可水解的酯基； R5和R6各自独立地是氢、C1-6烷基、C1-4烷氧基、羟乙基、叠氮乙基、氨基乙基，当R5是氢或C, -a烷基时，R6是羟基、C1-4烷氧基、氨基、C1-4烷基氨基、二(Ci-4.当 R5 为氢或 C-a烷基时，R6 为羟基、C1-4烷氧基、氨基、C1-4烷基氨基、二(Ci-4. )烷基氨基、取代的 C1-4 烷基，其中所述烷基取代基选自羟基、叠氮基、氨基、胍基、腈基、羧基、甲酰亚胺基和苯基，或氨基酸或肽的酰基残基；或 R5 和 R6，连同它们所连接的氮原子，是一个未取代或取代的杂环，具有 1 至 2 个环成员，且每个环中具有最多 4 个独立选自氧、氮和硫的杂原子，其中所述取代基选自由 C1-4 烷基、C1-4 烷氧基、三氟甲基、羟基、卤素、氨基、腈、羧基、氨基甲酰基、氨基甲酰基、C, -4 烷基氨基和氨基（C1-4）烷基组成的组；W 是直接键、氧、硫或 NR'°； Y 是氧或 NR10 Z 是氢、羟基、C1-4 烷基、C1-4 烷氧基、-NR7R8、氨基（C1-4）烷基、叠氮（C1-4）烷基或羟基（C1-4）烷基； R7 和 R8 各自独立地为氢、C1-4 烷基或烷酰基；以及 R10 是氢、C1-4 烷基、C1-4 烷基氨基或二(C1-4)烷基氨基； 或其无毒药学上可接受的盐，是新型抗菌剂，可用于治疗人类和其他动物的传染性疾病。此外，还公开了新型中间体及其制备工艺。
• A Novel Potent Nicotinamide Phosphoribosyltransferase Inhibitor Synthesized via Click Chemistry
  作者：Giampiero Colombano、Cristina Travelli、Ubaldina Galli、Antonio Caldarelli、Maria Giovanna Chini、Pier Luigi Canonico、Giovanni Sorba、Giuseppe Bifulco、Gian Cesare Tron、Armando A. Genazzani

  DOI：10.1021/jm9010669

  日期：2010.1.28

  The inhibition of NAD synthesis or salvage pathways has been proposed as a novel target for antitumoral drugs. Two molecules with this mechanism of action are at present undergoing clinical trials. In searching for similar novel molecules, we exploited copper-catalyzed [3 + 2] cycloaddition between azides and alkynes (click chemistry) to synthesize 185 novel analogues. The most promising compound displays an IC50 for cytotoxicity in vitro of 3.8 +/- 0.3 nM and an IC50 for NAD depletion of 3.0 +/- 0.4 nM. Herein, we strengthen previous data suggesting that this class of compounds induces autophagic cell death. In addition to characterizing this compound and providing a rationale via molecular docking, we reinforce the excellent potential of click chemistry for rapidly generating structure-activity relationships and for drug screening.
• US5672701A
  申请人：——

  公开号：US5672701A

  公开（公告）日：1997-09-30