马尿酰 N-羟基琥珀酰亚胺酯 | 66134-74-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 马尿酰 N-羟基琥珀酰亚胺酯
• 中文别名: 马尿酰N-羟基琥珀酰亚胺酯
• 英文名称: 2,5-dioxopyrrolidin-1-yl 2-benzamidoacetate
• 英文别名: Benzamide, N-(2-((2,5-dioxo-1-pyrrolidinyl)oxy)-2-oxoethyl)-；(2,5-dioxopyrrolidin-1-yl) 2-benzamidoacetate
• CAS: 66134-74-5
• 化学式: C₁₃H₁₂N₂O₅
• 分子量: 276.249
• InChiKey: YLQZGWYYLOQNEQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  马尿酰 N-羟基琥珀酰亚胺酯 、 N-ε-maleimido-L-lysine hydrochloride 在 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (2S)-2-[3-[(1R)-2-[[1-[(S)-5-(2-benzamidoacetamido)-5-carboxypentyl]-2,5-dioxopyrrolidin-3-yl]thio]-1-carboxyethyl]ureido]pentanedioic acid
  参考文献：
  名称：

  Preparation of Asymmetric Urea Derivatives that Target Prostate-Specific Membrane Antigen for SPECT Imaging

  摘要：

  Prostate-specific membrane antigen (PSMA) has been identified as a diagnostic and therapeutic target for prostate cancer. (S)-2-[3-[(R)-1-Carboxy-2-mercaptoethyl]ureido-pentanedioic acid (Cys-CO-Glu) were used to design novel PSMA targeting probes by nucleophilic conjugate addition between cysteine and maleimide based reagents. 3 ([I-123]IGLCE) was synthesized by this strategy and showed high affinity for PSMA. Results of binding inhibition assays of these derivatives suggested the importance of an aromatic group and succinimide moiety for high affinity. [I-123]3 was evaluated in vivo with PSMA positive LNCaP and PSMA negative PC-3 human prostate cancer xenograft bearing mice. [I-125]3 accumulated in LNCaP tumors but not in PC-3 tumors, and the accumulation was inhibited by 2-(phosphonomethyl)pentanedioic acid (2-PMPA). Use of [I-123]3 provided positive images of LNCaP tumors in single photon emission tomography scans. These results warrant further evaluation of [I-123]3 and its derivatives as radiolabeled probes for the diagnosis of prostate cancer.

  DOI：

  10.1021/jm400895s
• 作为产物：
  描述：

  苯甲酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.25h， 生成 马尿酰 N-羟基琥珀酰亚胺酯
  参考文献：
  名称：

  Preparation of Asymmetric Urea Derivatives that Target Prostate-Specific Membrane Antigen for SPECT Imaging

  摘要：

  Prostate-specific membrane antigen (PSMA) has been identified as a diagnostic and therapeutic target for prostate cancer. (S)-2-[3-[(R)-1-Carboxy-2-mercaptoethyl]ureido-pentanedioic acid (Cys-CO-Glu) were used to design novel PSMA targeting probes by nucleophilic conjugate addition between cysteine and maleimide based reagents. 3 ([I-123]IGLCE) was synthesized by this strategy and showed high affinity for PSMA. Results of binding inhibition assays of these derivatives suggested the importance of an aromatic group and succinimide moiety for high affinity. [I-123]3 was evaluated in vivo with PSMA positive LNCaP and PSMA negative PC-3 human prostate cancer xenograft bearing mice. [I-125]3 accumulated in LNCaP tumors but not in PC-3 tumors, and the accumulation was inhibited by 2-(phosphonomethyl)pentanedioic acid (2-PMPA). Use of [I-123]3 provided positive images of LNCaP tumors in single photon emission tomography scans. These results warrant further evaluation of [I-123]3 and its derivatives as radiolabeled probes for the diagnosis of prostate cancer.

  DOI：

  10.1021/jm400895s

文献信息

• Acyl, N-protected .alpha.-aminoacyl, and peptidyl derivatives as prodrug forms of the alcohol deterrent agent cyanamide
  作者：Chul Hoon Kwon、Herbert T. Nagasawa、Eugene G. DeMaster、Frances N. Shirota

  DOI：10.1021/jm00160a021

  日期：1986.10

  were synthesized specifically as prodrugs, including benzoylcyanamide (2), pivaloylcyanamide (3), and 1-adamantoylcyanamide (4), as well as long- and medium-chain fatty acyl derivatives such as palmitoyl- (6), stearoyl- (7), and n-butyrylcyanamide (5). N-Protected alpha-aminoacyl and peptidyl derivatives of cyanamide were also synthesized, and these include N-carbobenzoxyglycyl- (10), hippuryl- (13)

  氰胺（H2NC与N相同）是一种有效的醛脱氢酶（AlDH）抑制剂，在治疗上用作一种醇类威慑剂，已知会以乙酰氰胺的形式快速代谢并排泄到尿液中（1）。根据我们的观察结果，即1在体内被脱乙酰基化为氰胺，尽管非常轻微，从而作为后者的前药形式的前体，专门合成了几种氰胺的酰基衍生物作为前药，包括苯甲酰基氰酰胺（2），新戊酰氰胺（ 3），1-金刚烷基氨酰胺（4），以及长链和中链脂肪酰基衍生物，例如棕榈酰-（6），硬脂酰基-（7）和正丁酰氰胺（5）。还合成了N-保护的氰酰胺的α-氨基酰基和肽基衍生物，包括N-碳苯甲氧基甘氨酰-（10），马尿酰基-（13），N-苯甲酰基-L-亮氨酸-（14），N-碳苯甲氧基氧基-L-亮氨酰-（18），N-碳苯甲氧基-L-焦谷氨酰-（22），L-焦谷氨酰基-L-亮氨酰-（19）和L-焦谷氨酰基-L-苯丙氨酰氰胺（20）。腹膜内给药后3小时，所有这些氰胺前药在大鼠体内均显着提高了
• FUMARATE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USE
  申请人：Nguyen Mark Quang

  公开号：US20170022149A1

  公开（公告）日：2017-01-26

  Fumarate compounds, pharmaceutical compositions comprising the fumarate compounds, and methods of using fumarate compounds and pharmaceutical compositions for treating neurodegenerative, inflammatory, and autoimmune disorders including multiple sclerosis, psoriasis, irritable bowel disorder, ulcerative colitis, arthritis, chronic obstructive pulmonary disease, asthma, Parkinson's disease, Huntington's disease, and amyotrophic lateral sclerosis are disclosed.

  本文揭示了富马酸盐化合物、包括富马酸盐化合物的药物组合物，以及利用富马酸盐化合物和药物组合物治疗神经退行性、炎症性和自身免疫性疾病的方法，包括多发性硬化症、牛皮癣、肠易激综合征、溃疡性结肠炎、关节炎、慢性阻塞性肺病、哮喘、帕金森病、亨廷顿病和肌萎缩侧索硬化症。
• Bentley, John D.; Maclaren, John A., Australian Journal of Chemistry, 1991, vol. 44, # 4, p. 537 - 542
  作者：Bentley, John D.、Maclaren, John A.

  DOI：——

  日期：——
• Superactive GRF analogs
  申请人：ELI LILLY AND COMPANY

  公开号：EP0511003B1

  公开（公告）日：1999-03-24
• OKAI, XIDEHO;NODZE, YASUXARU
  作者：OKAI, XIDEHO、NODZE, YASUXARU

  DOI：——

  日期：——