5-anilino-3-methyl-5-oxopentanoic acid | 100823-19-6

• 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: 5-anilino-3-methyl-5-oxopentanoic acid
• 英文别名: 3-methyl-N-phenyl-glutaramic acid；3-Methyl-N-phenyl-glutaramidsaeure；β-Methyl-glutarsaeure-monoanilid
• CAS: 100823-19-6；100823-20-9；100823-21-0
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: YMHUFHFMJABSQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-anilino-3-methyl-5-oxopentanoic acid 在 palladium on activated charcoal chromium(III) oxide 、 氢氧化钾 、 sodium tetrahydroborate 、 Amberline IR 120B 、 氢气 、 sodium ethanolate 、 氯甲酸乙酯 、 溶剂黄146 、 lithium triethoxyaluminum hydride 、 三乙胺 、 三氯氧磷 作用下， 以 乙醚 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 123.17h， 生成 (R)-(+)-diethyl 3-methylhexadecanedioate
  参考文献：
  名称：

  Optical resolution of 3-methyl-N-phenylglutaramic acid and synthesis of optically active muscone

  摘要：

  DOI：

  10.1021/jo00384a054
• 作为产物：
  描述：

  3-甲基戊二酸酐 、 苯胺 在 Mycobacterium smegmatis acyltransferase 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 反应 2.0h， 以76%的产率得到5-anilino-3-methyl-5-oxopentanoic acid
  参考文献：
  名称：

  酶促酰胺键形成：通过耻垢分枝杆菌酰基转移酶合成氨基氧酸

  摘要：

  开发了一种基于使用耻垢分枝杆菌(MsAcT) 的酰基转移酶在水中制备氨基含氧酸的高效策略。从苯胺和一系列不同的酸酐开始，以优异的产率 (68–94%) 和快速反应 (0.5–5 h) 进行了 1 M 规模的生物转化。高底物催化剂比（M底物/ M催化剂：25 000）、酶稳定性（一个月没有任何活性损失）和出色的蛋白质纯化产量（从 2 克湿细胞糊中提取 130 毫克）使该工艺成为绿色、经济高效的方法，成功应用于制备SAHA合成的关键中间体。

  DOI：

  10.1039/d2gc00655c

文献信息

• Identification of novel quinazolinedione derivatives as RORγt inverse agonist
  作者：Yoshiyuki Fukase、Ayumu Sato、Yoshihide Tomata、Atsuko Ochida、Mitsunori Kono、Kazuko Yonemori、Keiko Koga、Toshitake Okui、Masashi Yamasaki、Yasushi Fujitani、Hideyuki Nakagawa、Ryoukichi Koyama、Masaharu Nakayama、Robert Skene、Bi-Ching Sang、Isaac Hoffman、Junya Shirai、Satoshi Yamamoto

  DOI：10.1016/j.bmc.2017.12.039

  日期：2018.2

  Novel small molecules were synthesized and evaluated as retinoic acid receptor-related orphan receptor-gamma t (ROR gamma t) inverse agonists for the treatment of inflammatory and autoimmune diseases. A hit compound, 1, was discovered by high-throughput screening of our compound library. The structure-activity relationship (SAR) study of compound 1 showed that the introduction of a chlorine group at the 3-position of 4-cyanophenyl moiety increased the potency and a 3-methylpentane-1,5-diamide linker is favorable for the activity. The carbazole moiety of 1 was also optimized; a quinazolinedione derivative 18i suppressed the increase of IL-17A mRNA level in the lymph node of a rat model of experimental autoimmune encephalomyelitis (EAE) upon oral administration. These results indicate that the novel quinazolinedione derivatives have great potential as orally available small-molecule ROR gamma t inverse agonists for the treatment of Th17-driven autoimmune diseases. A U-shaped bioactive conformation of this chemotype with ROR gamma t protein was also observed. (C) 2017 Elsevier Ltd. All rights reserved.
• Blaise; Gault, Bulletin de la Societe Chimique de France, 1907, vol. <4> 1, p. 91
  作者：Blaise、Gault

  DOI：——

  日期：——
• The Mitchell bunionectomy: A prospective study of 60 consecutive cases utilizing single K-wire fixation
  作者：Marco Teli、Federico A. Grassi、Carlo Montoli、Sergio Moalli、Ugo E. Pazzaglia

  DOI：10.1016/s1067-2516(01)80080-6

  日期：2001.5

  The authors prospectively evaluated 45 patients (60 feet) affected by hallux valgus and treated with a distal metatarsal osteotomy. The surgical procedure consisted of a modified Mitchell osteotomy, in which fixation was achieved with a Kirschner wire that was driven into the proximal osteotomy fragment and buttressed the distal one. Early weightbearing was allowed without a cast. Follow-up averaged 25 months. The mean American Orthopedic Foot and Ankle Society clinical hallux score increased from 44.6/100 preoperatively to 83.2/100. Radiographic evaluation showed that mean metatarsophalangeal and intermetatarsal angles decreased respectively from 31.7 degrees to 16.9 degrees, and from 15.4 degrees to 8.6 degrees. Short-term loss of correction occurred in three cases (4%). Six feet (10%) had unrelieved metatarsalgia that was related to excessive shortening of the first metatarsal and/or inappropriate orientation of the metatarsal head. Stabilization of the Mitchell osteotomy with a Kirschner wire proved safe and effective for the surgical correction of mild to moderate hallux valgus.
• JPS60156656A
  申请人：——

  公开号：JPS60156656A

  公开（公告）日：1985-08-16
• Optical resolution of 3-methyl-N-phenylglutaramic acid and synthesis of optically active muscone
  作者：Daiyo Terunuma、Masakazu Motegi、Makoto Tsuda、Takeshi Sawada、Hiromichi Nozawa、Hiroyuki Nohira

  DOI：10.1021/jo00384a054

  日期：1987.4