[2-Acetyloxy-4-(hydroxymethyl)phenyl] acetate | 113118-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: [2-Acetyloxy-4-(hydroxymethyl)phenyl] acetate
• CAS: 113118-24-4
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: ITZGFBXNXYRFCU-UHFFFAOYSA-N

物化性质

• 沸点：
  342.3±37.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-Acetyloxy-4-(hydroxymethyl)phenyl] acetate 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-(bromomethyl)-1,2-phenylene diacetate
  参考文献：
  名称：

  N- and C-terminal modifications of negamycin

  摘要：

  Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected beta-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50 = 2.3 muM), has antibacterial activity (Escherichia coli, MIC = 16 mug/mL), and is efficacious in an E. coli murine septicemia model (ED50 = 16.3 mg/kg). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00393-7
• 作为产物：
  描述：

  3,4-二乙酰氧基苯甲醛 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [2-Acetyloxy-4-(hydroxymethyl)phenyl] acetate
  参考文献：
  名称：

  N- and C-terminal modifications of negamycin

  摘要：

  Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected beta-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50 = 2.3 muM), has antibacterial activity (Escherichia coli, MIC = 16 mug/mL), and is efficacious in an E. coli murine septicemia model (ED50 = 16.3 mg/kg). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00393-7

文献信息

• Gyermek, Laszlo; Lee, Chingmuh; Cho, Young-Moon, Medicinal Chemistry Research, 2002, vol. 11, # 2, p. 116 - 136
  作者：Gyermek, Laszlo、Lee, Chingmuh、Cho, Young-Moon、Nguyen, Nguyen、Tsai, Shen-Kou

  DOI：——

  日期：——
• PRELIMINARY ANTIPROLIFERATIVE EVALUATION OF NATURAL,-SYNTHETIC BENZALDEHYDES AND BENZYL ALCOHOLS
  作者：ALEJANDRO MADRID、LUIS ESPINOZA、KAREN CATALÁN、CESAR GONZALEZ、IVÁN MONTENEGRO、MARCO MELLADO、ENRIQUE WERNER、MAURICIO CUELLAR、JOAN VILLENA

  DOI：10.4067/s0717-97072013000300003

  日期：——

  Vanillin, o-vanillin, natural and synthetic benzaldehydes and benzyl alcohols were assessed for antiproliferative effects using different human cell lines. Benzyl alcohols were synthesized from benzaldehydes reduced with NaBH4 in methanol solution. A new method for deprotection of ether compounds with TiCl4 solution was achieved with better performance, than previously reported. Twenty four compounds were tested. The in vitro growth inhibition assay was based on sulphorhodamine dye to quantify cell viability. Catechol 9 derived from piperonal as well as compounds 4 and 12 showed higher cytotoxicity on breast and prostate cancer cell lines (MDA-MB-231 and PC-3 respectively). o-Vanillin 5 has the highest cytotoxicity for all cell lines. IC50 values of 35.40 +/- 4.2 mu M Breast MDA-MB231; 47.10 +/- 3.8 mu M Prostate PC-3; 72.50 + 5.4 mu M Prostate DU-145; 85.10 +/- 6.5 mu M and Colon HT-29, were obtained without toxicity towards dermal human fibroblast (DHF cells).
• BETA-THIOPROPIONYL-AMINO ACID DERIVATIVES AND THEIR USE AS BETA-LACTAMASE INHIBITORS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0934262A1

  公开（公告）日：1999-08-11
• US6156774A
  申请人：——

  公开号：US6156774A

  公开（公告）日：2000-12-05
• [EN] BETA-THIOPROPIONYL-AMINO ACID DERIVATIVES AND THEIR USE AS BETA-LACTAMASE INHIBITORS<br/>[FR] DERIVES DE BETA-THIOPROPIONYL-AMINOACIDE ET UTILISATION DE CES DERNIERS EN TANT QU'INHIBITEURS DE BETA-LACTAMASE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1998017639A1

  公开（公告）日：1998-04-30

  (EN) Mercapto amino acid derivatives of formula (I), wherein R is hydrogen, a salt-forming cation of an $i(in vivo) hydrolysable ester-forming group; R1 is selected from (a) and (b) in which A is a monocyclic aryl or heteroaryl ring and B is a monocyclic aryl, alicyclic or heterocyclic ring, C and D are independently -Zp-(CR8CR9)q- or -(CR8CR9)q-Zp- where p is 0 or 1, q is 0 to 3 provided that p + q in C is not 0, R8 and R9 are independently hydrogen or (C1-6)alkyl or together represent oxo and Z is O, NR10 or S(O)x where R10 is hydrogen, (C1-6)alkyl or aryl(C1-6)alkyl and x is 0-2, and wherein C and D are linked ortho to one another on each of the rings A and B in formula (b); R2 is hydrogen, (C1-6)alkyl or aryl(C1-6)alkyl; R3 is hydrogen, (C1-6)alkyl optionally substituted by up to three halogen atoms, (C3-7)cycloalkyl, fused aryl(C3-7)cycloalkyl, (C3-7)cycloalkyl(C2-6)alkyl, (C2-6)alkenyl, (C2-6)alkynyl, aryl, aryl-(CH2)m-X-(CH2)n, heterocyclyl or heterocyclyl-(CH2)m-X-(CH2)n, where m is 0 to 3, n is 1 to 3 and X is O or S(O)x where x is 0-2 or a bond; R4 is hydrogen or an $i(in vivo) hydrolysable acyl group; and R5 and R6 are independently hydrogen and (C1-6)alkyl or together represent (CH2)r, where r is 2 to 5; for use in treatment of bacterial infections in humans or animals by administration in combination with a $g(b)-lactam antibiotic.(FR) Dérivés de mercapto aminoacide de formule (I), dans laquelle: R représente hydrogène, un cation formant un sel d'un groupe formant un ester hydrolysable $i(in vivo); R1 est sélectionné entre (a) et (b) dans lesquels A représente un anneau monocyclique aryle ou hétéroaryle et B représente un anneau monocyclique aryle ou un anneau alicyclique ou hétérocyclique; C et D représentent indépendamment -Zp-(CR8CR9)q- ou -(CR8CR9)q-Zp- dans lesquelles p vaut 0 ou 1, q vaut entre 0 et 3 à condition que p + q dans C ne soit pas égal à 0, R8 et R9 représentent indépendamment hydrogène ou alkyle (C1-6) ou bien représentent ensemble oxo et Z représente O, NR10 ou S(O)x où R10 représente hydrogène, alkyle (C1-6) ou aryle alkyle (C1-6) et x vaut entre 0 et 2; C et D sont liés l'un à l'autre par une liaison ortho sur chacun des anneaux A et B de la formule (b); R2 représente hydrogène, alkyle (C1-6) ou aryle alkyle (C1-6); R3 représente hydrogène, alkyle (C1-6) facultativement substitué par jusqu'à trois atomes halogène, cycloalkyle (C3-7), aryle (C3-7) cycloalkyle fusionné, cycloalkyle (C3-7) alkyle (C2-6), alcényle (C2-6), alcynyle (C2-6), aryle, aryle-(CH2)m-X-(CH2)n, hétérocyclyle ou hétérocyclyl-(CH2)m-X-(CH2)n, où m est compris entre 0 et 3, n est compris entre 1 et 3 et X représente O ou S(O)x où x est compris entre 0 et 2 ou bien représente une liaison; et R4 représente hydrogène ou un groupe acyle hydrolysable $i(in vivo); et R5 et R6 représentent indépendamment hydrogène et alkyle (C1-6) ou bien représentent ensemble (CH2)r, où r est compris entre 2 et 5. Ces dérivés sont utiles dans le traitement d'infections bactériennes chez l'homme ou l'animal par l'administration en combinaison avec un antibiotique de la famille des bêta-lactamines.