N-(3,4-dimethyl-phenyl)-glycine | 66947-34-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(3,4-dimethyl-phenyl)-glycine
• 英文别名: N-(3,4-Dimethyl-phenyl)-glycin；N-(3,4-dimethyl-phenyl)-glycine；2-(3,4-dimethylanilino)acetic acid
• CAS: 66947-34-0
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: QQYONWZDZSRKMD-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  375.9±30.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethyl-phenyl)-glycine 生成 3-(3,4-dimethylphenyl)sydnone
  参考文献：
  名称：

  双取代sydnones的合成和中枢神经系统抑制特性

  摘要：

  合成了许多未知的双取代 3-苯基sydnone 并进行了初步筛选。3-tolylsynones苯环中的甲基、溴和氯基团增强了CNS抑制作用，而sydnone环4-位的甲基不增加原始sydnone显示的CNS抑制作用。

  DOI：

  10.1002/ardp.19783110205
• 作为产物：
  描述：

  N-(3,4-dimethylphenyl)glycine ethyl ester 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 N-(3,4-dimethyl-phenyl)-glycine
  参考文献：
  名称：

  Harnessing Visible Light for the Synthesis of N‐Aryl Oxazolidines: Organocatalyzed Tandem Decarboxylation‐Cyclization

  摘要：

  摘要我们在此开发了一种有机光催化、可见光介导的串联脱羧-环化方法。以 Eosin-Y 作为有机光催化剂，驱动光氧化串联协议，在一次操作中构建 C-N、C-O 和 C-C 键。反应机理是先进行脱羧反应，然后由 N-芳基甘氨酸和甲醛形成氨基醇中间体，最后与另一种甲醛发生环化反应，生成 N-芳基恶唑烷衍生物。

  DOI：

  10.1002/adsc.202300889

文献信息

• 一种3-胺烷基色酮化合物及其制备方法
  申请人：东华理工大学

  公开号：CN113651788A

  公开（公告）日：2021-11-16

  本发明公开了一种3‑胺烷基色酮化合物及其制备方法，制备方法包括以下实验步骤：在室温下混合溶剂中，2‑羟基苯基烯胺酮和N‑芳基甘氨酸为反应底物，在18W蓝光照射下搅拌反应8‑12小时，至TLC检测原料转化完全，反应混合液经柱层析分离，可制得产物3‑胺烷基色酮化合物。
• Visible‐Light‐Enabled Photosensitizer‐ and Additive‐Free Decarboxylative Coupling Cyclization of Enaminone with <i>N</i> ‐Arylglycine for 3‐Aminoalkyl Chromones
  作者：Zhi‐Qiang Zhu、Jia‐Yu Hu、Zong‐Bo Xie、Juan Tang、Zhang‐Gao Le

  DOI：10.1002/adsc.202200304

  日期：2022.7.5

  An photosensitizer- and additive-free, visible-light-induced decarboxylative aminoalkylation/C−O coupling cyclization of enaminones with N-arylglycine for the synthesis of 3-aminoalkyl chromones has been achieved. This synthetic method features good functional-group tolerance, mild reaction conditions and no request of photocatalyst or additive, thus making this protocol more practical and sustainable

  已经实现了一种不含光敏剂和添加剂、可见光诱导的脱羧氨基烷基化/C-O 偶联环化烯胺酮与N-芳基甘氨酸合成 3-氨基烷基色酮的方法。该合成方法具有良好的官能团耐受性、反应条件温和、无需光催化剂或添加剂等特点，使该方案更具实用性和可持续性。
• FUSED IMIDAZOLE COMPOUND HAVING INDOLEAMINE 2,3-DIOXYGENASE INHIBITORY ACTIVITY
  申请人：Shenzhen Chipscreen Biosciences Co., Ltd.

  公开号：EP3560928A1

  公开（公告）日：2019-10-30

  The invention discloses a type of fused imidazole compound, preparation method and application thereof. The structure of the compound is shown in general formula I. The definition of each group therein is as described in the specification. These compounds are capable of selectively inhibiting indoleamine 2,3-dioxygenase (IDO). The compounds can act as an IDO inhibitor for treating and/or preventing a disease having a pathological feature with IDO-mediated tryptophan metabolic pathways, for example, cancer, eye disease, autoimmune disease, psychological disorder, depression symptom, anxiety disorder and other diseases.

  本发明公开了一种融合咪唑化合物及其制备方法和应用。该化合物的结构如通式 I 所示。其中各基团的定义如说明书所述。这些化合物能够选择性地抑制吲哚胺 2,3-二氧化酶（IDO）。这些化合物可作为 IDO 抑制剂，用于治疗和/或预防具有 IDO 介导的色氨酸代谢途径病理特征的疾病，例如癌症、眼病、自身免疫性疾病、心理障碍、抑郁症状、焦虑症和其他疾病。
• Fused imidazole compound having indoleamine 2,3-dioxygenase inhibitory activity
  申请人：SHENZHEN CHIPSCREEN BIOSCIENCES CO., LTD.

  公开号：US10604529B2

  公开（公告）日：2020-03-31

  The invention discloses a type of fused imidazole compound, preparation method and application thereof. The structure of the compound is shown in general formula I. The definition of each group therein is as described in the specification. These compounds are capable of selectively inhibiting indoleamine 2,3-dioxygenase (IDO). The compounds can act as an IDO inhibitor for treating and/or preventing a disease having a pathological feature with IDO-mediated tryptophan metabolic pathways, for example, cancer, eye disease, autoimmune disease, psychological disorder, depression symptom, anxiety disorder and other diseases.

  本发明公开了一种融合咪唑化合物及其制备方法和应用。该化合物的结构如通式 I 所示。其中各基团的定义如说明书所述。这些化合物能够选择性地抑制吲哚胺 2,3-二氧化酶（IDO）。这些化合物可作为 IDO 抑制剂，用于治疗和/或预防具有 IDO 介导的色氨酸代谢途径病理特征的疾病，例如癌症、眼病、自身免疫性疾病、心理障碍、抑郁症状、焦虑症和其他疾病。
• Substituted 3-(Phenylsulfonyl)-1-phenylimidazolidine-2,4-dione Derivatives as Novel Nonpeptide Inhibitors of Human Heart Chymase
  作者：Shinjiro Niwata、Harukazu Fukami、Motoo Sumida、Akiko Ito、Saki Kakutani、Masayuki Saitoh、Kenji Suzuki、Masahiro Imoto、Hiroshi Shibata、Seiichi Imajo、Yoshinobu Kiso、Takaharu Tanaka、Hiroshi Nakazato、Takafumi Ishihara、Shinji Takai、Daisuke Yamamoto、Naotaka Shiota、Mizuo Miyazaki、Hideki Okunishi、Akio Kinoshita、Hidenori Urata、Kikuo Arakawa

  DOI：10.1021/jm960793t

  日期：1997.7.1

  A series of 3-(phenylsulfonyl)-1-phenylimidazolidine-2,4-dione derivatives have been synthesized and evaluated for their ability to selectively inhibit human heart chymase. The structure-activity relationship studies on these compounds gave the following results. The 1-phenyl moiety participates in a hydrophobic interaction where an optimum size is required. At this position, 3,4-dimethylphenyl is the best moiety for inhibiting chymase and showed high selectivity compared with chymotrypsin and cathepsin G. A 3-phenylsulfonyl moiety substituted with hydrogen-bond accepters such as nitrile and methoxycarbonyl enhances its activity. Molecular-modeling studies on the interaction of 3-[(4-chlorophenyl)sulfonyl]-1-(4-chlorophenyl)imidazolidine-2,4-dione (29) with the active site of human heart chymase suggested that the 1-phenyl moiety interacts with the hydrophobic P-1 pocket, the 3-phenylsulfonyl moiety resides in the S-1'-S-2' subsites, and the 4-carbonyl of the imidazolidine ring and sulfonyl group interact with the oxyanion hole and the His-45 side chain of chymase, respectively. The complex model is consistent with the structure-activity relationships.