naphtho[2,3-d][1,3]dioxole-6-carboxylic acid | 5656-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphtho[2,3-d][1,3]dioxole-6-carboxylic acid
• 英文别名: naphtho[2,3-d]-1,3-dioxole-6-carboxylic acid；2H-Naphtho[2,3-D][1,3]dioxole-6-carboxylic acid；benzo[f][1,3]benzodioxole-6-carboxylic acid
• CAS: 5656-50-8
• 化学式: C₁₂H₈O₄
• 分子量: 216.193
• InChiKey: DABGBTRNBKBSCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 、 二正丙胺 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到N,N-dipropylnaphtho[2,3-d][1,3]dioxole-6-carboxamide
  参考文献：
  名称：

  Efficient Modulation of γ-Aminobutyric Acid Type A Receptors by Piperine Derivatives

  摘要：

  Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates gamma-aminobutyric acid type A receptors (GABA(A)R). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABA(A)R by means of a two-microelectrode voltage-clamp technique. GABA(A)R were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABA(A)R. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABA(A) (maximal GABA-induced chloride current modulation (IGABA-max = 1673% +/- 146%, EC50 = 51.7 +/- 9.5 mu M), while 25 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC50 = 13.8 +/- 1.8 mu M, IGABA-max = 760% +/- 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA(A)R modulators.

  DOI：

  10.1021/jm5002277
• 作为产物：
  描述：

  5,6-双(溴甲基)-1,3-苯并二氧杂环戊烯 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 naphtho[2,3-d][1,3]dioxole-6-carboxylic acid
  参考文献：
  名称：

  Efficient Modulation of γ-Aminobutyric Acid Type A Receptors by Piperine Derivatives

  摘要：

  Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates gamma-aminobutyric acid type A receptors (GABA(A)R). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABA(A)R by means of a two-microelectrode voltage-clamp technique. GABA(A)R were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABA(A)R. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABA(A) (maximal GABA-induced chloride current modulation (IGABA-max = 1673% +/- 146%, EC50 = 51.7 +/- 9.5 mu M), while 25 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC50 = 13.8 +/- 1.8 mu M, IGABA-max = 760% +/- 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA(A)R modulators.

  DOI：

  10.1021/jm5002277

文献信息

• TEAGUE, S. J.;ROTH, G. P., SYNTHESIS, BRD, 1986, N 5, 427-429
  作者：TEAGUE, S. J.、ROTH, G. P.

  DOI：——

  日期：——
• RESIST UNDERLAYER FILM-FORMING COMPOSITION AND METHOD FOR FORMING RESIST PATTERN USING THE SAME
  申请人：NISSAN CHEMICAL CORPORATION

  公开号：US20210397090A1

  公开（公告）日：2021-12-23

  A composition for forming a resist underlayer film enables the formation of a desired resist pattern; and a method for forming a resist pattern using this resist underlayer film forming composition. A resist underlayer film forming composition contains an organic solvent and a polymer that has a structure represented by formula (1) or (2) at an end of the polymer chain. (In formula (1) and formula (2), X represents a divalent organic group; A represents an aryl group having 6-40 carbon atoms; R1 represents a halogen atom, an alkyl group having 1-40 carbon atoms or an alkoxy group having 1-40 carbon atoms; each of R2 and R3 independently represents a hydrogen atom, an optionally substituted alkyl group having 1-10 carbon atoms, an aryl group having 6-40 carbon atoms or a halogen atom; each of n1 and n3 independently represents an integer of 1-12; and n2 represents an integer of 0-11.)
• US4958010A
  申请人：——

  公开号：US4958010A

  公开（公告）日：1990-09-18
• Efficient Modulation of γ-Aminobutyric Acid Type A Receptors by Piperine Derivatives
  作者：Angela Schöffmann、Laurin Wimmer、Daria Goldmann、Sophia Khom、Juliane Hintersteiner、Igor Baburin、Thomas Schwarz、Michael Hintersteininger、Peter Pakfeifer、Mouhssin Oufir、Matthias Hamburger、Thomas Erker、Gerhard F. Ecker、Marko D. Mihovilovic、Steffen Hering

  DOI：10.1021/jm5002277

  日期：2014.7.10

  Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates gamma-aminobutyric acid type A receptors (GABA(A)R). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABA(A)R by means of a two-microelectrode voltage-clamp technique. GABA(A)R were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABA(A)R. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABA(A) (maximal GABA-induced chloride current modulation (IGABA-max = 1673% +/- 146%, EC50 = 51.7 +/- 9.5 mu M), while 25 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC50 = 13.8 +/- 1.8 mu M, IGABA-max = 760% +/- 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA(A)R modulators.