2-propyl-4-benzyl-1,2,4-thiadiazolidine-3,5-dione | 1332857-06-3

• 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: 2-propyl-4-benzyl-1,2,4-thiadiazolidine-3,5-dione
• 英文别名: 4-Benzyl-2-propyl-1,2,4-thiadiazolidine-3,5-dione
• CAS: 1332857-06-3
• 化学式: C₁₂H₁₄N₂O₂S
• 分子量: 250.321
• InChiKey: MGYLROLZHGUZBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异氰酸丙酯 、 异硫氰酸苯甲酯 在 磺酰氯 作用下， 以 乙醚 为溶剂， 以72%的产率得到2-propyl-4-benzyl-1,2,4-thiadiazolidine-3,5-dione
  参考文献：
  名称：

  Discovery of 1,2,4-thiadiazolidine-3,5-dione analogs that exhibit unusual and selective rapid cell death kinetics against acute myelogenous leukemia cells in culture

  摘要：

  4-Benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione (TDZD-8) was previously identified as an antileukemic agent exhibiting no evident toxicity toward normal hematopoietic cells. An SAR study has been carried out to examine the effect of varying the C-2 and C-4- substituents on the thiadiazolidinone ring of TDZD-8 on antileukemic activity. These studies resulted in the identification of more druglike analogs that exhibited comparable potency to TDZD-8 in killing acute myelogenous leukemia (AML) cells in culture. Surprisingly, the cell death kinetics induced by several of these novel analogs on MV-411 cells were extremely fast, with commitment to death occurring within 30 min. At a concentration of 10 mu M, 3f (LD50 = 3.5 mu M) completely eradicated cell viability of MV-411 cells within 2 h, while analog 3e (LD50 = 2.0 mu M) decimated cell viability within 30 min at a concentration of 10 mu M and effectively abolished cell viability at 5 mu M within 1-2 h. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.027

文献信息

• [EN] NOVEL TDZD ANALOGS AS AGENTS THAT DELAY, PREVENT, OR REVERSE AGE-ASSOCIATED DISEASES; AND AS ANTI-CANCER AND ANTILEUKEMIC AGENTS<br/>[FR] NOUVEAUX ANALOGUES DE TDZD EN TANT QU'AGENTS QUI RETARDENT, PRÉVIENNENT OU INVERSENT DES MALADIES ASSOCIÉES À L'ÂGE; ET EN TANT QU'AGENTS ANTICANCÉREUX ET ANTILEUCÉMIQUES
  申请人：BOWROJU SURESH KUARM

  公开号：WO2021163572A1

  公开（公告）日：2021-08-19

  The present disclosure is concerned with TDZD analogs for the treatment of various neurodegenerative diseases such as sarcopenia, supranuclear palsy, Alzheimer´s disease, Parkinson´s disease, Huntington´s disease, and dementia, and various cancers such as, for example, sarcomas, carcinomas, hematological cancers, solid tumors, breast cancer, cervical cancer, gastrointestinal cancer, colorectal cancer, brain cancer, skin cancer, prostate cancer, ovarian cancer, bladder cancer, thyroid cancer, testicular cancer, pancreatic cancer, endometrial cancer, melanomas, gliomas, leukemias, lymphomas, chronic myeloproliferative disorders, myelodysplastic syndromes, myeloproliferative neoplasms, and plasma cell neoplasms (myelomas). This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本公开涉及用于治疗各种神经退行性疾病，例如肌肉减少症、核上性瘫痪、阿尔茨海默病、帕金森病、亨廷顿病和痴呆，以及各种癌症，例如肉瘤、癌、血液肿瘤、实体肿瘤、乳腺癌、宫颈癌、胃肠癌、结直肠癌、脑癌、皮肤癌、前列腺癌、卵巢癌、膀胱癌、甲状腺癌、睾丸癌、胰腺癌、子宫内膜癌、黑色素瘤、神经胶质瘤、白血病、淋巴瘤、慢性骨髓增殖性疾病、骨髓增生异常综合征、骨髓增殖性肿瘤和浆细胞肿瘤（骨髓瘤）的TDZD类似物。本摘要旨在作为在特定技术领域内进行搜索的扫描工具，并不是用来限制本发明的。
• Discovery of 1,2,4-thiadiazolidine-3,5-dione analogs that exhibit unusual and selective rapid cell death kinetics against acute myelogenous leukemia cells in culture
  作者：Shama Nasim、Monica L. Guzman、Craig T. Jordan、Peter A. Crooks

  DOI：10.1016/j.bmcl.2011.06.027

  日期：2011.8

  4-Benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione (TDZD-8) was previously identified as an antileukemic agent exhibiting no evident toxicity toward normal hematopoietic cells. An SAR study has been carried out to examine the effect of varying the C-2 and C-4- substituents on the thiadiazolidinone ring of TDZD-8 on antileukemic activity. These studies resulted in the identification of more druglike analogs that exhibited comparable potency to TDZD-8 in killing acute myelogenous leukemia (AML) cells in culture. Surprisingly, the cell death kinetics induced by several of these novel analogs on MV-411 cells were extremely fast, with commitment to death occurring within 30 min. At a concentration of 10 mu M, 3f (LD50 = 3.5 mu M) completely eradicated cell viability of MV-411 cells within 2 h, while analog 3e (LD50 = 2.0 mu M) decimated cell viability within 30 min at a concentration of 10 mu M and effectively abolished cell viability at 5 mu M within 1-2 h. (C) 2011 Elsevier Ltd. All rights reserved.