3-(2,5-dioxo-2,5-dihydropyrrole-1-yl)propionaldehyde | 25441-46-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-(2,5-dioxo-2,5-dihydropyrrole-1-yl)propionaldehyde
• 英文别名: 3-(2,5-dioxo-2,5-dihydropyrrol-1-yl)propionaldehyde；3-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanal；3-(2,5-dioxopyrrol-1-yl)propanal
• CAS: 25441-46-7
• 化学式: C₇H₇NO₃
• 分子量: 153.137
• InChiKey: BUKJIMFRGCHNGI-UHFFFAOYSA-N

物化性质

• 沸点：
  296.4±23.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,5-dioxo-2,5-dihydropyrrole-1-yl)propionaldehyde 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 2.0h， 生成 (2R)-2-amino-3-[1-[3-[[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxan-4-yl]amino]propyl]-2,5-dioxopyrrolidin-3-yl]sulfanylpropanoic acid
  参考文献：
  名称：

  The design, synthesis, and evaluation of two universal doxorubicin-linkers: Preparation of conjugates that retain topoisomerase II activity

  摘要：

  The design, synthesis, and evaluation of two N-alkylmaleimide aldehydes have been achieved, which upon reductive alkylation with the C3'-amino group of doxorubicin (DOX) permits the preparation of DOX conjugates via Michael addition of thiol-containing vectors. This method enables the mild, facile, and high-throughput preparation of DOX conjugates that retain the basic C3'-nitrogen, a pre-requisite for topoisomerase II inhibition. Seven DOX-amino acid conjugates were prepared, each displaying similar inhibitory activity as the parent drug. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.046
• 作为产物：
  描述：

  1-(3-hydroxypropyl)-1H-pyrrole-2,5-dione 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以55.7%的产率得到3-(2,5-dioxo-2,5-dihydropyrrole-1-yl)propionaldehyde
  参考文献：
  名称：

  The design, synthesis, and evaluation of two universal doxorubicin-linkers: Preparation of conjugates that retain topoisomerase II activity

  摘要：

  The design, synthesis, and evaluation of two N-alkylmaleimide aldehydes have been achieved, which upon reductive alkylation with the C3'-amino group of doxorubicin (DOX) permits the preparation of DOX conjugates via Michael addition of thiol-containing vectors. This method enables the mild, facile, and high-throughput preparation of DOX conjugates that retain the basic C3'-nitrogen, a pre-requisite for topoisomerase II inhibition. Seven DOX-amino acid conjugates were prepared, each displaying similar inhibitory activity as the parent drug. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.046

文献信息

• ANTI-CD228 ANTIBODIES AND ANTIBODY-DRUG CONJUGATES
  申请人：Seattle Genetics, Inc.

  公开号：US20200246479A1

  公开（公告）日：2020-08-06

  Provided are novel anti-CD228 antibodies and antibody-drug conjugates and methods of using such anti-CD228 antibodies and antibody-drug conjugates to treat cancer.

  提供了新型抗CD228抗体和抗体药物结合物，以及使用这些抗CD228抗体和抗体药物结合物来治疗癌症的方法。
• [EN] NEW IMMUNOSTIMULATORS AND USE THEREOF IN IMMUNOTHERAPY<br/>[FR] NOUVEAUX IMMUNOSTIMULATEURS ET LEUR UTILISATION EN IMMUNOTHÉRAPIE
  申请人：UNIV NANTES

  公开号：WO2021140203A1

  公开（公告）日：2021-07-15

  The present invention relates to a new family of iNKT stimulators, referred to as 6"-O-PEGm-NHR-GalCer, which are potent analogues of KRN7000. These iNKT stimulators can advantageously be used in therapy, in particular for the prevention and/or treatment of many diseases requiring a stimulation of an immune response, such as cancer, viral, bacterial or parasitic diseases, autoimmune diseases or inflammatory diseases. The iNKT cell stimulator of the invention may be coupled to a biological carrier, such as a therapeutic and/or targeting agent, or be vectorized, for example in nanoparticles, to be specifically delivered to target cells.

  本发明涉及一种新的iNKT刺激剂家族，称为6"-O-PEGm-NHR-GalCer，它是KRN7000的有效类似物。这些iNKT刺激剂可以优势地用于治疗，特别是用于预防和/或治疗需要刺激免疫反应的许多疾病，如癌症、病毒、细菌或寄生虫病、自身免疫性疾病或炎症性疾病。本发明的iNKT细胞刺激剂可以与生物载体（如治疗和/或靶向剂）耦合，或者被载体化，例如在纳米粒子中，以专门传递到目标细胞。
• [EN] FUNCTIONALIZED THIENO-INDOLE DERIVATIVES FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS THIÉNO-INDOLES FONCTIONNALISÉS POUR LE TRAITEMENT DU CANCER
  申请人：NERVIANO MEDICAL SCIENCES SRL

  公开号：WO2013149946A1

  公开（公告）日：2013-10-10

  The invention relates to new functionalized thieno-indole derivatives of formula (I) or (II) which have cytotoxic activity and are useful in treating diseases such as cancer and cellular proliferation disorders. The invention also relates to the use of these functionalized thieno-indole derivatives in the preparation of conjugates. Formula (I) or (II) wherein R1 and R2 taken together form a group (D) or (G): wherein R5 is hydrogen or C1-C4 alkyl; R3 and R4 are independently hydrogen, C1-C4 alkyl or C1-C4 hydroxyalkyi; n is 0, 1 or 2; each of X is independently -O-, -S- or -NR4-; each of Y is independently -CH = or -N=; R7 and R8 are independently hydrogen, halogen, hydroxy, C1-C4 alkoxy, cyano, -NHCOOR3, -C(NH)NH2 or -NR3R4; A is -O-, -NH- or -CO-; L is null or a conditionally-cleavable moiety; W is null or a self-immolative moiety comprising one or more self-immolative groups; Z is null or a peptidic, non peptidic or hybrid peptidic and non peptidic linker; RM is null or a reactive moiety; R6 is a leaving group; A1 is null or A; L1 is hydrogen or L.

  本发明涉及具有细胞毒性活性的新型功能化噻吩吲衍生物（式（I）或（II）），并可用于治疗癌症和细胞增殖紊乱等疾病。本发明还涉及使用这些功能化噻吩吲衍生物制备共轭物。其中R1和R2共同形成一个基团（D）或（G）：其中R5为氢或C1-C4烷基；R3和R4独立地为氢、C1-C4烷基或C1-C4羟基烷基；n为0、1或2；每个X独立地为-O-、-S-或-NR4-；每个Y独立地为-CH=或-N=；R7和R8独立地为氢、卤素、羟基、C1-C4烷氧基、氰基、-NHCOOR3、-C（NH）NH2或-NR3R4；A为-O-、-NH-或-CO-；L为空或有条件可割离的基团；W为空或包含一个或多个自解离基团的自解离基团；Z为空或为肽、非肽或混合肽和非肽连接基团；RM为空或为反应性基团；R6为离去基团；A1为空或为A；L1为氢或L。
• [EN] LIPID CONJUGATES FOR THE DELIVERY OF THERAPEUTIC AGENTS<br/>[FR] CONJUGUÉS LIPIDIQUES POUR L'ADMINISTRATION D'AGENTS THÉRAPEUTIQUES
  申请人：ARROWHEAD PHARMACEUTICALS INC

  公开号：WO2022056273A1

  公开（公告）日：2022-03-17

  Disclosed herein are compounds according to Formula (I) comprising PK/PD modulators for delivery of oligonucleotide-based agents, e.g., double stranded RNAi agents, to certain cell types, such for example skeletal muscle cells, in vivo. The PK/PD modulators disclosed herein, when conjugated to an oligonucleotide-based therapeutic or diagnostic agent, such as an RNAi agent, can enhance the delivery of the composition to the specified cells being targeted to facilitate the inhibition of gene expression in those cells.

  本文公开了公式（I）中的化合物，包括PK/PD调节剂，用于将基于寡核苷酸的制剂（例如双链RNAi制剂）递送到体内某些细胞类型，例如骨骼肌细胞。本文所披露的PK/PD调节剂与基于寡核苷酸的治疗或诊断制剂（如RNAi制剂）结合后，可以增强将该组合物递送到特定的目标细胞，以促进在这些细胞中抑制基因表达。
• Small molecule compositions and methods for increasing drug efficiency using compositions thereof
  申请人：Castellino John Angelo

  公开号：US20050148534A1

  公开（公告）日：2005-07-07

  In certain embodiments, provided herein are compositions and methods for increasing drug efficiency. The conjugates provided are in certain embodiments, for compositions and methods in treatment of variety of diseases and have the formula 1: D-L-S  (1) or formula 2: D-L-S′  (2) wherein D is a drug moiety; L, which may or may not be present, is a non-releasing linker moiety; S is a substrate for a kinase, other than a hexokinase, a protein kinase or a lipid kinase; and S′ is a substrate for a phosphotransferase, other than a hexokinase, a protein kinase or a lipid kinase.

  在某些实施例中，本文提供了增加药物效率的组合物和方法。所提供的共轭物在某些实施例中，用于治疗各种疾病的组合物和方法，其具有以下公式1：D-L-S（1）或公式2：D-L-S'（2），其中D是药物基团；L是非释放连接基团，可以存在也可以不存在；S是激酶底物，不包括己糖激酶、蛋白激酶或脂肪激酶；S'是磷酸转移酶底物，不包括己糖激酶、蛋白激酶或脂肪激酶。