4-acetylaminophthalic acid diethyl ester | 149967-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-acetylaminophthalic acid diethyl ester
• 英文别名: 4-acetylamino-phthalic acid diethyl ester；4-Acetylamino-phthalsaeure-diaethylester；4-Acetamino-phthalsaeure-diaethylester；4-(Acetylamino)-1,2-benzenedicarboxylic acid, diethyl ester；diethyl 4-acetamidobenzene-1,2-dicarboxylate
• CAS: 149967-20-4
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: BRIREEWXZWYHNV-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  435.0±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetylaminophthalic acid diethyl ester 在 lithium hydroxide 、 copper(l) iodide 、 四丁基碘化铵 、 铜 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二丁醚 、 环己酮 为溶剂， 反应 132.5h， 生成 4-[4-carboxy-N-[6-(3,5-didecoxyphenoxy)hexanoyl]anilino]phthalic acid
  参考文献：
  名称：

  A Novel Class of Potent Nonglycosidic and Nonpeptidic Pan-Selectin Inhibitors

  摘要：

  An early step of the inflammatory response, the rolling of leukocytes on activated endothelial cells, is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialy Lewis(x) is a ligand for E-, P-, and L-selectin and therefore serves as a lead structure for the development of analogues. A combination of synthesis and structure-based design allowed rapid optimization. The current lead 2a was evaluated in our E-selectin cell flow chamber assay where it proved to inhibit rolling and adhesion with an IC50 of 28 +/- 7 mu M. The assays used are predictive for the in vivo efficacy of test compounds as shown for 2a in a proteose peptone induced peritonitis model of acute inflammation in mice.

  DOI：

  10.1021/jm060468y
• 作为产物：
  描述：

  4-nitrophthalic acid diethyl ester 在 sodium tetrahydroborate 、 溶剂黄146 、 iron(II) chloride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 4-acetylaminophthalic acid diethyl ester
  参考文献：
  名称：

  A Novel Class of Potent Nonglycosidic and Nonpeptidic Pan-Selectin Inhibitors

  摘要：

  An early step of the inflammatory response, the rolling of leukocytes on activated endothelial cells, is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialy Lewis(x) is a ligand for E-, P-, and L-selectin and therefore serves as a lead structure for the development of analogues. A combination of synthesis and structure-based design allowed rapid optimization. The current lead 2a was evaluated in our E-selectin cell flow chamber assay where it proved to inhibit rolling and adhesion with an IC50 of 28 +/- 7 mu M. The assays used are predictive for the in vivo efficacy of test compounds as shown for 2a in a proteose peptone induced peritonitis model of acute inflammation in mice.

  DOI：

  10.1021/jm060468y

文献信息

• Cyclic imide derivatives, compositions and use
  申请人：Glaxo Inc.

  公开号：US05252560A1

  公开（公告）日：1993-10-12

  Compounds are described of the formula ##STR1## wherein: R.sup.1 is C.sub.3-6 alkyl or C.sub.1-3 alkylthioC.sub.1-3 alkyl; R.sup.2 is an optionally substituted C.sub.1-6 alkyl or C.sub.1-6 alkoxy group, aryl, heteroaryl, arylC.sub.1-4 alkyl, heteroarylC.sub.1-4 alkyl or a side-chain of a natural .alpha.-amino acid; R.sup.3 is hydrogen, C.sub.1-6 alkyl, CHR.sup.4 COR.sup.5 (where R.sup.4 is a side-chain of a natural .alpha.-amino acid and R.sup.5 is hydroxyl, C.sub.1-6 alkoxy or NHR.sup.6 where R.sup.6 represents a hydrogen atom or a C.sub.1-6 alkyl group) or a group (CH.sub.2).sub.n X (where n is 1 to 6 and X is hydroxyl, C.sub.1-4 alkoxy, heteroaryl or a group NR.sup.7 R.sup.8 where R.sup.7 and R.sup.8 are each hydrogen or C.sub.1-6 alkyl or the group NR.sup.7 R.sup.8 forms a 5 to 7 membered cyclic amine); and Het is an optionally substituted cyclic imide where the cyclic imide ring system has the formula (i), (ii) or (iii) ##STR2## in which A, B, C and D are each CH or 1 or 2 of A, B, C and D represents N and the others represent CH, and E and F may each independently represent CH or N; and physiologically acceptable salts and solvates thereof. These compounds inhibit metalloproteases involved in tissue degradation. Compounds of the invention may be formulated for use in a variety of conditions involving tissue degradation including arthropathy, dermatological conditions, bone resorption, inflammatory diseases, tumour invasion and multiple sclerosis and related diseases involving myelin degradation, and in the promotion of wound healing.

  该文描述了公式## STR1 ##的化合物，其中：R.sup.1是C.sub.3-6烷基或C.sub.1-3烷硫基C.sub.1-3烷基; R.sup.2是可选取代的C.sub.1-6烷基或C.sub.1-6烷氧基，芳基，杂芳基，芳基C.sub.1-4烷基，杂芳基C.sub.1-4烷基或天然α-氨基酸的侧链; R.sup.3是氢，C.sub.1-6烷基，CHR.sup.4COR.sup.5（其中R.sup.4是天然α-氨基酸的侧链，R.sup.5是羟基，C.sub.1-6烷氧基或NHR.sup.6，其中R.sup.6表示氢原子或C.sub.1-6烷基）或(CH.sub.2).sub.nX（其中n为1至6，X为羟基，C.sub.1-4烷氧基，杂芳基或基团NR.sup.7R.sup.8，其中R.sup.7和R.sup.8均为氢或C.sub.1-6烷基或基团NR.sup.7R.sup.8形成5至7成员环状胺）;和Het是可选取代的环酰亚胺，其中环酰亚胺环系统具有公式（i），（ii）或（iii）##STR2##其中A、B、C和D分别为CH或1或2个A、B、C和D表示N，其他表示CH，E和F可以各自独立地表示CH或N;以及其生理上可接受的盐和溶剂化物。这些化合物抑制了参与组织降解的金属蛋白酶。发明的化合物可制成用于各种涉及组织降解的情况的配方，包括关节病，皮肤病，骨吸收，炎症性疾病，肿瘤侵袭和多发性硬化症以及涉及髓鞘降解的相关疾病，并用于促进伤口愈合。
• 77. Nitrosoacylarylamines. Part III. A new method of preparation
  作者：H. France、I. M. Heilbron、D. H. Hey

  DOI：10.1039/jr9400000369

  日期：——
• Haworth et al., Journal of the Chemical Society, 1945, p. 409,411
  作者：Haworth et al.

  DOI：——

  日期：——
• Miller, Justus Liebigs Annalen der Chemie, 1881, vol. 208, p. 230
  作者：Miller

  DOI：——

  日期：——